Reactivity of DonorâAcceptor Cyclopropanes ... - Wiley Online Library

Review DOI: 10.1002/ijch.201500100

Reactivity of Donor-Acceptor Cyclopropanes with Saturated and Unsaturated Heterocyclic Compounds Ashok Kumar Pandey, Asit Ghosh, and Prabal Banerjee*[a] Abstract: Strain in the ring engenders versatile reactivity that can be utilized for the synthesis of complex molecules by the assimilation of suitable substituents. In this context, vicinal donor-acceptor cyclopropanes (DACs) serve as threecarbon synthetic equivalents in organic synthesis from the last few decades. Owing to their zwitterionic nature, they

have been frequently utilized in [3 + n]-annulation reactions with different dipolarophiles like aldehydes, imines, oximes, epoxides, aziridines, etc. This review highlights developed synthetic tools for annulation reactions of vicinal donor-acceptor cyclopropanes with saturated and unsaturated heterocyclic compounds.

Keywords: annulation, · donor-acceptor cyclopropanes, · heterocycles, · strained rings

1. Introduction The beauty of organic synthesis persists in developing new methodologies for the construction of heterocycles of significant interest. Synthetic designs are developed based on the feasibility of the reaction, applying the basic principle of making highly reactive systems (strained molecules incorporated with reactive functional groups). It is quite well known that donor-acceptor cyclopropanes a (DACs) have acted as one of the most efficient threecarbon synthetic equivalents for the construction of complex molecules over the past few decades.[1] Installation of donor and acceptor groups at the vicinal position of cyclopropane has proven to be most appropriate for C¢C bond cleavage, resulting in the formation of reactive 1,3zwitterion b (Scheme 1). Consequently, it has been utilized as a versatile building block for the synthesis of multiple heterocycles employing different dipolarophiles. DACs react with a variety of dipolarophiles, like aldehydes,[2] ketones,[3] imines, oximes, heterocumulenes, nitrones, etc.[4] and have led to the formation of five- or sixmembered heterocycles. They have also shown valuable reactivity with strained heterocycles,[5,6] as well as five- or six-membered heterocycles.[7–21] The beauty of DAC reactions is the formation of monocyclic/bicyclic five- or sixmembered heterocycles, which can be used for the design of several bioactive molecules (Scheme 1). Most of these reactions proceed through formal annulation pathways catalyzed by different Lewis acids. Synergistic polarization of the DAC C¢C bond in the presence of Lewis acids plays a key role in these types of formal annulation reactions. This review will demonstrate the reactivity of DACs with different heterocycles to afford important heterocyclic scaffolds. Further, the reactivity will be elaborated with different pathways to get high stereoselectivity in Isr. J. Chem. 2016, 56, 512 – 521

Scheme 1. Annulations of DAC with acyclic and cyclic dipolarophiles.

the product formation, and their use in total synthesis, as well. The purpose of this review is to present the importance of DAC annulations with different reactive heterocycles and their possible application to uninvestigated heterocycles. [a] A. K. Pandey, A. Ghosh, P. Banerjee Department of Chemistry Indian Institute of Technology Ropar Nangal Road Rupnagar Punjab-140001 (India) Fax: (+ 91) 1881 223395http://www.iitrpr.ac.in/chemistry/praba e-mail: [email protected]

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Review 2. Annulation Reactions of Donor-acceptor Cyclopropanes with Heterocycles 2.1 Annulations with Cyclic Nitronates

In 2013, Tabolin and Loffe et al. synthesized bicyclic nitrosoacetates 3 and 4 by using annulation reactions of DACs 1 with six-membered cyclic nitronates 2 (Scheme 2).[22] The reaction was performed in anhydrous conditions employing 4 è MS and anhydrous Lewis acids, because hydrated Lewis acids, e.g., Yb(OTf)3.6H2O, decreased the yield of the annulated product, presumably due to partial hydrolysis of the starting nitronates. Reactions showed compatibility with a variety of nitronates Dr. Prabal Banerjee was born in 1975 in Burdwan (West Bengal, India). He obtained his doctoral degree from NCL, Pune (India) and later worked as postdoctoral fellow in the RWTH Aachen University, Germany, and Purdue University, USA, before joining IIT Ropar as an assistant professor in the Department of Chemistry. He has extensive research experience in pericyclic reactions, with special emphasis on annulation reactions, asymmetric catalysis, and synthesis of medicinally significant molecules. Most recently, he has been involved in the study of the reactivity of different strained rings towards annulation reactions for the synthesis of pharmaceutically important heterocyclic compounds. Ashok K. Pandey was born in Jaunpur (U.P. India) in 1987. He obtained his M.Sc. degree in organic chemistry from the University of Allahabad (U.P. India) in 2010. He then joined the group of Dr. P. Banerjee at the Indian Institute of Technology Ropar, Punjab (Punjab, India), to carry out Ph.D. work on the synthesis of heterocyclic scaffolds found in several bioactive molecules by using annulations of donor-acceptor cyclopropanes with strained rings. Asit Ghosh was born in Birbhum (West Bengal, India) in 1988. He received his M.Sc. degree in organic chemistry from Gauhati University (Assam, India) in 2012. In 2013, he joined the group of Dr. P. Banerjee at the Indian Institute of Technology Ropar, Punjab (India) and is pursuing graduate work on the annulation of strained rings for the construction of heterocycles having structural scaffolds of bioactive molecules.

Isr. J. Chem. 2016, 56, 512 – 521

Scheme 2. [3 + 3]-Annulation of DACs with nitronates.

and DACs. However, the diastereoselectivity of the reaction depended upon the nitronate structure. 2.2 Annulations with Cyclic Azomethine Imines

Charette et al. reported for the first time [3 + 3]-annulation reactions of DACs 5 with azomethine imine 6 for dihydroquinoline 7 synthesis.[5] Later, Tang and coworkers successfully achieved high enantioselectivity in product formation using a chiral bisoxazoline (BOX) ligand (Scheme 3).[6] The side arm of the BOX ligand L1 played a significant role in obtaining high enantioselectivity.

Scheme 3. [3 + 3]-Annulation of DACs with azomethine imines.

Recently, Guo and coworkers reported similar reactivity of dicyanomethanides 8 towards [3 + 3]-annulation with DACs 9, resulting in the formation of 3,4-dihydro-1Hpyrido[2,–1a]phthalazine derivatives 10 (Scheme 4).[7]

2.3 Annulations with Strained Heterocycles

Heteroatom-containing strained rings, like epoxides and aziridines, are highly reactive to behave as dipolarophiles in the presence of Lewis acids. DACs have been employed as three-carbon synthons, both in intermolecular and intramolecular fashions, with these strained rings to obtain valuable molecular structures. Ó 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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Review generated in situ from the epoxide, via Meinwald rearrangement, which led to intermediate (iii). Intermediate (iii) underwent C¢C bond installation to produce the desired product 13. 2.3.1.2 Intramolecular Reactions

Scheme 4. [3 + 3]-Annulation of DACs with phthalazonium-dicyanomethanides.

2.3.1 Annulations with Epoxides 2.3.1.1 Intermolecular Reactions

The annulation reaction of DAC 11 with epoxide 12 led to the formation of THF derivatives 13 (Scheme 5).[8] The reaction entirely depended upon the presence of Lewis acids, solvents, and the temperature of the reaction medium. Epoxides, in the presence of Lewis acids, underwent Meinwald rearrangement, followed by [3 + 2]-annulation with DACs. The reaction was highly diastereoselective, and formation of cis-2,5-disubstituted THF deriva-

Wang et al. reported an intramolecular [3 + 2]-annulation reaction between epoxide and DAC 15 via Meinwald rearrangement to synthesize a bridged oxa-[3.2.1] skeleton, 16 (Scheme 6).[9] In this transformation, both Lewis acids and Brønsted acids were able to catalyze the reaction. Both terminal and internal epoxides with alkyl or aryl substituents underwent intramolecular cyclization with the DAC moiety of the molecule. The yield of the products varied from 37 % to 97 %, depending upon the different substituents present in the starting material.

Scheme 6. Intramolecular annulation of DAC with epoxide.

2.3.2 Annulations with Aziridines

Scheme 5. Intermolecular [3 + 2]-annulation reaction of DACs and epoxides.

Recently, our group developed an efficient MgI2-catalyzed annulation between DACs 17 and N-tosylaziridine dicarboxylate 18 to access highly substituted 2H-furo[2,– 3c]pyrrole 19 (Scheme 7).[10] The presence of two rings and four stereocenters, including one quaternary carbon stereocenter, in the product makes it a useful precursor for the synthesis of biologically active compounds like IKM-159, 20. The reaction showed Lewis-acid selectivity, and gave the desired product only with MgI2 and GaCl3. However, MgI2 gave the best yield, rather than GaCl3. Other Mg-containing Lewis acids, like MgBr2 and

tives 13 was observed, with both DAC and epoxide variants. The best yield for the formation of THF derivatives was observed with InCl3 as the Lewis acid in dichloroethane at 50 8C. The temperature played an important role in product formation. High temperature promoted decomposition of the reactants, and low temperature dramatically slowed down the rate of reaction. Epoxides having an aryl substituent gave THF with 50–88 % yield, with partially or highly electron-rich aryl group-bearing DACs. However, epoxides with aryl groups having electron-withdrawing functionality, or aliphatic groups, were not able to give the desired product. Lewis acid-catalyzed ring-opened intermediate (ii) of the DAC underwent a formal [3 + 2]-annulation reaction with aldehyde 14,

Scheme 7. [3 + 2]-Annulation of DACs with aziridines.

Isr. J. Chem. 2016, 56, 512 – 521



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Review Mg(OTf)2, failed to catalyze the reaction, and 20 mol % of MgI2 gave the best yield of the product, while higher loading of the catalyst enhanced the decomposition of reactants, and lower loading of the catalyst reduced the rate of annulation. Electron-rich aryl-bearing DACs and aziridines gave good yield of annulated products. In this transformation, DAC 17 undergoes rapid nucleophilic ring opening, assisted by iodide to give unstable ring-opened intermediate (iv). Intermediate (iv) subsequently attacks the activated aziridines (v), leading to the generation of key intermediate (vi). In this condition, two possible pathways are open for cyclization, according to BaldwinÏs rule. However, the 5-exo-trig cyclization (pathway a) is favored over 6-exo-tet cyclization (pathway b), due to the faster formation of the five-membered ring. After the 5-exo-trig cyclization, intermediate (vi) achieves a conformation favorable to undergo intramolecular cyclization in SN2 fashion, resulting in the formation of fused bicycle 19 (Scheme 8).

are also recognized for annulation reactions with heterocyclic compounds. In this context, Pagenkopf et al. have developed a method for the synthesis of fused tri- or tetracyclic moieties 23 employing [3 + 2]-annulation reactions of DAC 21 with indole derivatives 22 (Scheme 9).[11]

Scheme 9. Intermolecular [3 + 2]-annulation of DACs with indoles.

In this transformation, Me3SiOTf was used as the Lewis acid for activation of DACs in nitromethane. The reaction was highly efficient and stereochemically controlled. A single stereocenter on the DACs controls the diastereoselective formation of four new stereocenters. Reactions showed wide substrate scope for both reactants. Generally, electron-rich DACs gave 90 % yield of indole adducts. The diastereoselectivity of the annulation reaction was observed at low temperature (¢18 8C), whereas loss of selectivity was noticed at increased temperature. 2.4.1.2 Intramolecular Reactions

France and coworkers have developed a Lewis acid-catalyzed intramolecular ring-opening and cyclization reaction of DACs with the indole moiety 24 to access heterocyclic scaffolds 25 (Scheme 10).[12] This method involved the ring opening of a DAC, followed by Friedel-Crafts alkylation with a five-membered indole ring. A Lewis acid activated DAC 24 to give the ring-opened intermediate (viii) that underwent intramolecular Friedel-Crafts alkylaScheme 8. Proposed reaction mechanism for formation of 19.

2.4 Annulations with Five- or Six-membered Heterocycles

Donor-acceptor cyclopropanes also showed multifaceted reactivity towards annulation reactions with unsaturated five- or six-membered heterocycles. These heterocycles may be indole moieties, tetrahydrofurans, benzofurans, pyridines, and pyrazolines. Both intermolecular and intramolecular reactions of DACs with some of these rings are known. 2.4.1 Annulations with Indoles 2.4.1.1 Intermolecular Reactions

In contrast to aryl groups as donating groups in DACs, heteroatom-bearing electron-donating groups in DACs Isr. J. Chem. 2016, 56, 512 – 521

Scheme 10. Intramolecular [3 + 2]-annulation of DACs with indoles.



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Review tion to form the desired product through intermediate (ix). This transformation specifically generated the lactam ring portion of the hydropyrido[1,–2a]indole-6(7H)-ones 25. In(OTf)3 was an effective catalyst for the six-membered ring formation. It was used in 30 mol%, either in dichloromethane at room temperature or in 1,2-dichloroethane under reflux conditions. Electron-rich cyclopropanes cyclized efficiently with the indole moiety to produce 99 % yield of 25. Product yield varied from 50 % to 99 %, depending on the presence of substituents in the cyclopropane and indole moieties of the molecule. The electron-withdrawing substituent, i.e., the p-nitrophenyl group in cyclopropane, decreased the product yield, due to destabilization of the carbocation in ring-opened intermediate (viii). Monosubstitution in cyclopropane favored a better yield of the product, rather than disubstitution. This might be due to the steric hindrance that hindered the cyclization step.

ents in the DACs. When the DAC : furan ratio was 2 : 1, a double [3 + 2]-annulation reaction ensured the formation of adduct 29 in good yield, irrespective of the nature of the aryl group present in the DACs. In contrast, when an excess of furan was taken, the initial product 28 of the reaction, between 2,5-dimethylfuran and 2-phenyl DAC, interacted with the second furan molecule to give 30 through Lewis acid-induced Friedel-Crafts alkylation. 2,5Diphenylfuran failed to produce any annulated product in the reactions with 2-phenyl DAC, but yielded the product 31, following Friedel-Crafts alkylation on the bcarbon atom. 2.4.3 Cycloadditions with Benzofuran

Evanova et al.[18] reported [4 + 3]-cycloaddition reactions of DACs 32 with benzofuran derivative 33 under Lewis acid-catalyzed reaction conditions (Scheme 12). This was

2.4.2 Annulations with Furans

Furan can participate in reactions as a 4p unit, as well as a 2p unit. Indeed, examples of [1 + 2]-,[13] [2 + 2]-,[14] [3 + 2]-,[15] and [4 + 2]-annulations[16] to the C(2)¢C(3) furan bond, as well as formation of several bisadducts were described. Budynina et al. successfully investigated the reaction of different furan derivatives with DACs aiming to determine the preferable mode of interactions based on the nature of the substituents present in the furans and cyclopropanes (Scheme 11).[17] DACs 26 reacted with 2,5-dimethylfuran 27 in [3 + 2]annulation fashion, adding to the C(2)¢C(3) bond. The vinyl ether moiety present in the product 28 can be further transformed into another product, 29, depending on the ratio of the reagents and the nature of the substitu-

Scheme 11. Different modes of annulations of DACs with furans. Isr. J. Chem. 2016, 56, 512 – 521

Scheme 12. [4 + 3]-cycloaddition reaction of DACs with benzofurane derivatives.

the first example of a [4 + 3]-cycloaddition reaction of a DAC, where the DAC acted as a three-carbon synthetic equivalent, and a fused-furan derivative was used as a four-carbon synthetic equivalent. The substrate scope of the DACs and benzofuran derivatives was examined at standardized reaction conditions, and it was found that exo-product 34 was formed predominantly, in comparison with endo-product 35. Progress of the reaction depended on the reaction temperature, and high temperatures reduced product yield. This might be due to decomposition of the reactants at high temperature, however, at low temperature, decomposition was diminished, but yield of the product reduced. The best yield for the annulation reaction was achieved at room temperature. A 2-thienyl substituent in cyclopropane gave an excellent yield of products. p-Fluorophenyl-substituted cyclopropane was found to be more reactive than the phenyl DAC. Experimental observations and NMR spectroscopic data of the less-stable exo-isomer 34 supported a concerted reaction mechanism of the titled transformation (Scheme 13). The formation of the less-stable exo-isomer as the major product is further supported by the quantum-chemical calculations, as well as the results obtained



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Scheme 13. Reaction mechanism for formation of 35.

from the reaction between DACs and benzofuran at higher temperatures. The major exo-isomer decomposed during prolonged heating in the presence of the catalyst. 2.4.4 Annulations with Pyridines

Pagenkopf and coworkers reported an unique annulation reaction of DACs 36 with electron-deficient pyridine 37 to access functionalized indolizine derivatives 39, followed by MnO2 oxidation (Scheme 14).[19] Me3SiOTf was found to be the active catalyst for this transformation.

Scheme 15. Different modes of reactions of DACs with pyrazolines.

Scheme 14. [3 + 2]-Annulation of DACs with pyridines.

The purple-colored 2,3-dihydroindolizines 38 obtained from the reaction between DACs and the pyridine derivative was highly air sensitive. Therefore, to facilitate isolation and characterization, the annulated product 38 was immediately submitted to oxidation with MnO2. Electrondeficient pyridine gave good yield of the product, with alkyl or aryl substituent-bearing DACs. Electron-rich pyridine derivatives gave complex mixtures with DACs under the same reaction conditions. 2.4.5 Annulations with Pyrazolines

Tamilov et al. demonstrated reactions of DACs with 2pyrazoline derivatives towards formation of annulated and ring-opened products (Scheme 15).[20] In this case too, the reaction was controlled by Lewis acids, temperature, and substituents. In this study, reactivity of DACs and types of product formation entirely depended on the presence of Lewis acids and their amount, the quantity of Isr. J. Chem. 2016, 56, 512 – 521

reactants and their substituents, and the reaction temperature. The DAC 40 reacted with 2-pyrazolines 41 to give diazabicyclooctane derivatives 43 (57–61 %) in the presence of Sc(OTf)3 at 20 8C, whereas with 1-pyrazolines 42, predominantly pyrazoline derivatives 44 (yields 61–66 %) were formed. Anhydrous GaCl3 also catalyzed the reaction with both pyrazolines 41 and 42 towards formation of the product 44. However, a low temperature (0–5 8C) and an equimolar amount of GaCl3 with respect to the starting cyclopropane were required. When the temperature was increased from 0 to 40 8C, an excess amount of DAC 40 in the presence of GaCl3 reacted with pyrazolines 41 and 42 to produce 2-pyrazolines 45 and 46 in 1 : 1 ratio. 2.5 Asymmetric Synthesis

Asymmetric synthesis using chiral metal complexes has gained considerable attention in last few decades, and contributed to the art of organic synthesis, leading to the formation of important molecules. In chiral Lewis-acid catalysis, catalysts with metal cations form chiral complexes by coordinating with optically active ligands. Such types of complex have at least one vacant site suitable for coordination and activation of the substrates.[21] BOX and TOX (trisoxazoline) ligands are one of the most popular



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Review classes of chiral ligands, having all the requirements that satisfy chiral catalysis in organic synthesis.[23] There are several reports available in the literature concerning the asymmetric synthesis of molecules from annulation reactions of DACs with various dipolarophiles using different Lewis acids and optically active ligands.[24] In the following discussion, we will discuss some recent examples for asymmetric reactions of DACs with strained and five- or six-membered heterocyclic rings.

2.5.1 Reactions with Indoles

Asymmetric annulation reactions of DACs 47 with indoles 48 were reported by Tang and coworkers in 2013 (Table 1).[25] In this transformation, different BOX and TOX ligands were applied with Cu(OTf)2 Lewis acid under nitrogen atmosphere at room temperature. In a variety of BOX ligands, different yields and enantiomeric excesses (ee) of products were observed, depending upon different R1 and R2 substituents present in the ligand molecules. Ligand L4 gave better yield and ee of the product, in comparison with ligand L3 (Table 1, entries 1 and 2). The yield and ee of the product increased when ligands L4 to L7 were employed under the standardized reaction conditions (Table 1, entries 2 to 5). Scope of this transformation was also checked by a TOX ligand L8. The rate of the reaction was dramatically slowed down with this TOX ligand, and gave moderate yield and ee of the product (Table 1, entry 6).

Table 1. Asymmetric

synthesis

of

DAC

with

2.5.2 Reactions with Epoxides

Recently, our group developed an asymmetric approach for the synthesis of enantioenriched tetrahydrofurans from annulation of DACs with epoxides (Scheme 16).[8] In this context, a variety of BOX ligands (L9 to L12) were used with InCl3 at room temperature. The cyclopropane 50 was taken as a model for the study of an asymmetric transformation of the tandem cyclization reaction of a DAC and epoxide 51 into enantiomerically enriched THF derivative, 52. When the reaction was performed separately with ligands L9, L10, and L11 in the presence of InCl3, formation of the desired product was not observed, even after 15 days stirring at rt. However, the PyBOX ligand L12 with InCl3 gave a 66 : 34 enantiomeric ratio of the product in 68 % yield within 4 days at room temperature (Scheme 16). The failure of reaction with L9, L10, and L11 might be due to the sterically hindered tert-butyl group and spatial organization of the phenyl groups.

indoles.

Scheme 16. Asymmetric synthesis with a DAC and epoxide.

2.6 Applications in Total Synthesis 2.6.1 Synthesis of ( )-Deethyleburnamonine

Entry

Ligand R1 R2

1 2 3 4 5

Me Me Bn Bn Bn

6

Me

H (L3) Bn (L4) Bn (L5) 4-tBuC6H4CH2 (L6) 3,5-tBuC6H3CH2 (L7)

Isr. J. Chem. 2016, 56, 512 – 521

Time (h) Yield (%)

ee (%)

24 2 2 2 5

86 93 88 94 93

55 80 63 86 88

30

76

68

()-Deethyleburnamonine is a biologically active alkaloid.[26] There are number of methods reported for its synthesis, but all methods follow long routes. ()-Deethyleburnamonine was most recently synthesized by Lounasmaa in nine steps, with an overall yield of ~ 18–20 %.[27] Towards the development of an economical and short route for the synthesis of ()-deethyleburnamonine, France et al. developed a method using indium(III)catalyzed intramolecular tandem ring-opening/FriedelCrafts alkylation of donor-acceptor cyclopropane (Scheme 17).[28] Cyclopropane derivative 53 was subjected to cyclization reaction in the presence of 30 mol% InCl3 and led to cyclized product 54 in 71 % yield. When 54 was subjected to TFA hydrolysis, deprotection of the



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Scheme 17. Total synthesis of ()-deethyleburnamonine.

Boc-group ensued, along with C¢N bond formation, and gave ()-deethyleburnamonine derivatives 55 in 87 % yield. Finally, a Krapcho decarboxylation reaction[29] of 55 provided the desired ()-deethyleburnamonine 56. 2.6.2 Synthesis of ( )-Epimeloscine and ( )-Meloscine

Meloscine is one of the most common representatives of the Melodinus alkaloids.[30] Recently, Curran and coworkers synthesized ()-epimeloscine and ()-meloscine by using tandem radical intramolecular cyclization of DAC, followed by ring-closing metathesis (RCM).[31] When cyclopropane derivative 57 was subjected to radical cyclization, catalyzed by tributyltin hydride and AIBN at reflux conditions in toluene, 58 was formed in 38 % yield (Scheme 18). Boc-deprotection and allylation of compound 58 gave 59 in 73 % yield. Compound 59, subjected to RCM with the second generation Grubbs-Hoveyda catalyst, gave ()-epimeloscine 60 in 89 % yield. Epimerization of compound 60 with KOtBu provided ()-meloscine 61 in 83 % yield.

3. Outlook Functional groups with opposite electronic effects present in cyclopropanes at adjacent positions, i.e., donor-acceptor cyclopropanes synergistically polarize the C¢C bond of the ring to impart its significant reactivity. DACs have the tendency to behave as a three-carbon synthetic equivalent, and are involved in [3 + n]-annulation reactions with various dipolarophiles, ylides, and heterocycles. Both intermolecular and intramolecular annulations of DACs, with saturated and unsaturated heterocyclic compounds, make it an indispensable synthetic tool for the construction of complex molecules. The key importance of DACs is the formation of cyclic or bicyclic five/six-membered heterocyclic rings with good stereoselectivity. Asymmetric Isr. J. Chem. 2016, 56, 512 – 521

Scheme 18. Total synthesis of ()-meloscine.

synthesis using DACs has further added feathers to its application in organic synthesis. Although numerous approaches have been established by utilizing DACs towards new methodology development, as well as in the total synthesis of bioactive molecules, a lot of chemistry is restricted to various other dipolarophiles and strained rings. Asymmetric synthesis using DACs requires more attention to improve the enantioselectivity and diastereoselectivity, as not much chemistry is being developed using a variety of chiral ligands. Therefore, this field needs more conscious attention from organic chemists.

Acknowledgements We thank DST-India (SR/FT/CS-84/2010) for financial support to do the research work. A.K.P. and A.G. thank CSIR, New Delhi, and IIT Ropar, India, respectively, for their research fellowships.

References [1] a) E. Wenkert, Acc. Chem. Res. 1980, 13, 27 – 3; b) H. U. Reissig, Top. Curr. Chem. 1988, 144, 73 – 135; c) H. U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151 – 1196; d) M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321 – 347; e) M. A. Carson, C. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051 – 3060; f) F. De Simone, J. Waser, Synthesis 2009, 3353 – 3374; g) M. J. Campbell, J. S. Johnson, A. T. Parsons, P. D. Pohlhaus, S. D. Sanders, J. Org. Chem. 2010, 75, 6317 – 6325; h) T. P. Lebold, M. A. Kerr, Pure Appl. Chem. 2010, 82, 1797 – 1812; i) M. Y. Mel’nikov, E. M. Budynina, O. A. Iva-



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[2]

[3]

[4]

[5] [6] [7] [8] [9] [10] [11] [12] [13]

nova, I. V. Trushkov, Mendeleev Commun. 2011, 21, 293 – 301; j) Z. Wang, Synlett 2012, 2311 – 2327; k) M. A. Cavitt, L. H. Phun, S. France, Chem. Soc. Rev. 2014, 43, 804 – 818; l) T. F. Schneider, J. Kaschel, D. B. Werz, Angew. Chem. Int. Ed. 2014, 53, 5504 – 5523; m) H. K. Grover, M. R. Emmett, M. A. Kerr, Org. Biomol. Chem. 2015, 13, 655 – 671. a) P. D. Pohlhaus, J. S. Johnson, J. Org. Chem. 2005, 70, 1057 – 1059; b) P. D. Pohlhaus, J. S. Johnson, J. Am. Chem. Soc. 2005, 127, 16014 – 16015; c) P. D. Pohlhaus, S. D. Sanders, A. T. Parsons, W. Li, J. S. Johnson, J. Am. Chem. Soc. 2008, 130, 8642 – 8650; d) A. T. Parsons, M. J. Campbell, J. S. Johnson, Org. Lett. 2008, 10, 2541 – 2544; e) A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc. 2009, 131, 3122 – 3123; f) F. Benfatti, F. de Nanteuil, J. Waser, Org. Lett. 2012, 14, 386 – 389; g) F. de Nanteuil, E. Serrano, D. Perrotta, J. Waser, J. Am. Chem. Soc. 2014, 136, 6239 – 6242; h) S. D. Sanders, A. R. Olalla, J. S. Johnson, Chem. Commun. 2009, 5135 – 5137; i) G. Yang, Y. Shen, K. Li, Y. Sun, Y. Hua, J. Org. Chem. 2011, 76, 229 – 233; j) G. Yang, Y. Sun, Y. Shen, Z. Chai, S. Zhou, J. Chu, J. Chai, J. Org. Chem. 2013, 78, 5393 – 5400; k) A. G. Smith, M. C. Slade, J. S. Johnson, Org. Lett. 2011, 13, 1996 – 1999; l) S. Haubenreisser, P. Hensenne, S. Schroder, M. Niggemann, Org. Lett. 2013, 15, 2262 – 2265. a) F. Benfatti, F. de Nanteuil, J. Waser, Chem. Eur. J. 2012, 18, 4844 – 4849; b) T. Shiba, D. Kuroda, T. Kurahashi, S. Matsubara, Synlett. 2014, 25, 2005 – 2008; c) K. Kawai, I. Yokoe, Y. Sugita, Heterocycles 2000, 53, 657 – 664; d) A. R. Rivero, I. Feranandez, C. R. de Arellano, M. A. Sierra, J. Org. Chem. 2015, 80, 1207 – 1213; e) G. Yang, T. Wang, J. Chai, Z. Chai, Eur. J. Org. Chem. 2015, 1040 – 1046. a) X. Ma, Q. Tang, J. Ke, X. Yang, J. Zhang, H. Shao, Org. Lett. 2013, 15, 5170 – 5173; b) S. W. Wang, W. S. Guo, L. R. Wen, M. Li, RSC Adv. 2015, 5, 47418 – 47421; c) A. Karadeolian, M. A. Kerr, Angew. Chem. Int. Ed. 2010, 49, 1133 – 1135; d) B. Hu, S. Y. Xing, J. Ren, Z. W. Wang, Tetrahedron 2010, 66, 5671 – 5674; e) M. J. Campbell, J. S. Johnson, J. Am. Chem. Soc. 2009, 131, 10370 – 10371; f) C. A. Carson, M. A. Kerr, J. Org. Chem. 2005, 70, 8242 – 8244; g) Y. B. Kang, Y. Tang, X. L. Sun, Org. Biomol. Chem. 2006, 4, 299 – 301; h) A. T. Parsons, A. G. Smith, A. J. Neel, J. S. Johnson, J. Am. Chem. Soc. 2010, 132, 9688 – 9692; i) S. K. Jackson, A. Karadeolian, A. B. Driega, M. A. Kerr, J. Am. Chem. Soc. 2008, 130, 4196 – 4201; j) A. F. G. Goldberg, N. R. O. Connor, R. A. Craig II, B. M. Stoltz, Org. Lett. 2012, 14, 5314 – 5317. C. Perreault, S. R. Goudreau, L. E. Zimmer, A. B. Charette, Org. Lett. 2008, 10, 689 – 692. Y.-Y. Zhou, J. Li, L. Ling, S.-H. Liao, X.-L. Sun, Y.-X. Li, L.-J. Wang, Y. Tang, Angew. Chem. Int. Ed. 2013, 52, 1452 – 1456. H. Liu, C. Yuan, Y. Wu, Y. Xiao, H. Guo, Org. Lett. 2015, 17, 4220 – 4223. A. K. Pandey, A. Ghosh, P. Banerjee, Eur. J. Org. Chem. 2015, 2517 – 2523. W. Zhu, J. Ren, Z. Wang, Eur. J. Org. Chem. 2014, 3561 – 3564. A. Ghosh, A. K. Pandey, P. Banerjee, J. Org. Chem. 2015, 80, 7235 – 7242. B. Bajtos, M. Yu, H. Zhao, B. L. Pagenkopf, J. Am. Chem. Soc. 2007, 129, 9631 – 9634. D. V. Patil, M. A. Cavitt, P. Grzybowski. S. France, Chem. Commun. 2011, 47, 10278 – 10280. a) C. Boehm, O. Reiser, Org. Lett. 2001, 3, 1315 – 1318; b) P. C. Shieh, C. W. Ong, Tetrahedron 2001, 57, 7303 – 7307;

Isr. J. Chem. 2016, 56, 512 – 521

[14]

[15]

[16]

[17] [18] [19]

[20] [21]

[22] [23]

[24] [25] [26] [27]

c) R. B. Chhor, B. Nosse, S. Soergel, C. Boehm, M. Seitz, O. Reiser, Chem. Eur. J. 2003, 9, 260 – 270; d) B. Nosse, R. B. Chhor, W. B. Jeong, C. Boehm, O. Reiser, Org. Lett. 2003, 5, 941 – 944; e) M. Schinnerl, C. Boehm, M. Seitz, O. Reiser, Tetrahedron: Asymmetry 2003, 14, 765 – 771; f) E. Jezek, A. Schall, P. Kreitmeier, O. Reiser, Synlett 2005, 915 – 918; g) S. J. Hedley, D. L. Ventura, P. M. Dominiak, C. L. Nygren, H. M. L. Davies, J. Org. Chem. 2006, 71, 5349 – 5356. a) S. L. Schreiber, D. Desmaele, J. A. Porco, Tetrahedron Lett. 1988, 29, 6689 – 6692; b) T. S. Cantrell, A. C. Allen, H. Ziffer, J. Org. Chem. 1989, 54, 140 – 145; c) M. T. Crimmins, J. B. Thomas, Tetrahedron Lett. 1989, 30, 5997 – 6000; d) D. Sampedro, A. Soldevilla, P. J. Campos, R. Ruiz, M. A. Rodriguez, J. Org. Chem. 2008, 73, 8331 – 8336. a) P. J. Zimmermann, I. Blanarikova, V. Jaeger, Angew. Chem. Int. Ed. 2000, 39, 910 – 912; b) D. Berard, A. Jean, S. Canesi, Tetrahedron Lett. 2007, 48, 8238 – 8241; c) D. Berard, M.-A. Giroux, L. Racicot, C. Sabot, S. Canesi, Tetrahedron 2008, 64, 7537 – 7544. a) Y. Matsuya, K. Sasaki, M. Nagaoka, H. Kakuda, N. Toyooka, N. Imanishi, H. Ochiai, H. Nemoto, J. Org. Chem. 2004, 69, 7989 – 7993; b) C. Della Rosa, M. N. Kneeteman, P. M. E. Mancini, Tetrahedron Lett. 2005, 46, 8711 – 8714; c) V. Bagutski, A. de Meijere, Adv. Synth. Catal. 2007, 349, 1247 – 1255. A. O. Chagarovskiy, E. M. Budynina, O. A. Ivanova, Y. K. Grishin, I. V. Trushkov, P. V. Verteletskii, Tetrahedron, 2009, 65, 5385 – 5392. O. A. Ivanova, E. M. Budynina, Y. K. Grishin, I. V. Trushkov, P. V. Verteletskii, Angew. Chem. Int. Ed. 2008, 47, 1107 – 1110. a) N. A. Morra, C. L. Morales, B. Bajtos, X. Wang, H. Jang, J. Wang, M. Yu, B. L. Pagenkopf, Adv. Synth. Catal. 2006, 348, 2385 – 2390; b) R. A. Novikov, Y. V. Tomilov, O. M. Nefedov, Russ. Chem. Bull. 2012, 61, 1917 – 1924. Y. V. Tomilov, R. A. Novikov, O. Nefedov, Tetrahedron 2010, 66, 9151 – 9158. a) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999; b) Catalytic Asymmetric Synthesis, 2nd Edition (Ed.: I. Ojima), Wiley, New York, 2000; c) New Frontiers in Asymmetric Catalysis (Eds.: K. Mikami, M. Lautens), John Wiley & Sons, Hoboken, 2007. E. O. Gorbacheva, A. A. Tabolin, R. A. Novikov, Y. A. Khumutova, Y. V. Nelyubina, Y. V. Tomilov, S. L. Ioffe, Org. Lett. 2013, 15, 350 – 353. a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325 – 335; b) H. A. McManus, P. J. Guiry, Chem. Rev. 2004, 104, 4151 – 4202; c) G. Desimoni, G. Faita, K. A. Jorgensen, Chem. Rev. 2006, 106, 3561 – 3651; d) G. C. Hargaden, P. J. Guiry, Chem. Rev. 2009, 109, 2505 – 2550. A. T. Parson, J. S. Johnson, J. Am. Chem. Soc. 2009, 131, 3122 – 3123. H. Xiong, H. Xu, S. Liao, Z. Xie, Y. Tang, J. Am. Chem. Soc. 2013, 135, 7851 ¢ 7854. a) A. R. Stoit, U. K. Pandit, Tetrahedron, 1989, 45, 849 – 850; b) L. Szporny, Actual. Pharm. 1977, 29, 87 – 89. a) M. Lounasmaa, D. D. Belle, A. Tolvanen, Heterocycles, 1999, 51, 1125 – 1130; b) M. Lounasmaa, M. Berner, M. Brunner, H. Suomalainen, A. Tolvanen, Tetrahedron, 1998, 54, 10205 – 10216; c) M. Lounasmaa, L. Miikki, A. Tolvanen, Tetrahedron, 1996, 52, 9925 – 9930; d) A. R. Stoit, U. K.



520

Review Pandit, Tetrahedron, 1989, 45, 849 – 854; e) H. P. Husson, T. Imbert, C. Thal, P. Potier, Bull. Soc. Chim. Fr. 1973, 2013. [28] D. V. Patil, M. A. Cavitt, S. France, Heterocycles, 2012, 84, 1363 – 1373. [29] A. P. Krapcho, ARKIVOC, 2007, 1 – 53. [30] a) K. Bernauer, G. Englert, W. Vetter, E. Weiss, Helv. Chim. Acta 1969, 52, 1886 – 1905; b) W. E. Oberhaensli, Helv. Chim. Acta 1969, 52, 1905 – 1911; c) M. Daudon, H. Mehri,

Isr. J. Chem. 2016, 56, 512 – 521

M. M. Plat, E. W. Hagaman, F. M. Schell, E. Wenkert, J. Org. Chem. 1975, 40, 2838 – 2839. [31] H. Zhang, D. P. Curran, J. Am. Chem. Soc. 2011, 133, 10376 – 10378.


Received: November 30, 2015 Accepted: February 29, 2016 Published online: April 7, 2016


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Reactivity of DonorâAcceptor Cyclopropanes ... - Wiley Online Library

Reactivity of DonorâAcceptor Cyclopropanes ... - Wiley Online Library

Reactivity of DonorâAcceptor Cyclopropanes ... - Wiley Online Library

Reactivity of DonorâAcceptor Cyclopropanes ... - Wiley Online Library