Optimization studies for the ruthenium(II)-catalyzed direct ... - Nature

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MS (EI) m/z (relative intensity): 176 (21) [M]+, 161 (100) [M–Me]+, 133 (23) [M–Ac]+, 115. (8). ...... MS (LIFDI) m/z calcd for [C32H44O4Ru]+ 594.2, found 594.1.
Supplementary Table 1: Optimization studies for the ruthenium(II)-catalyzed direct meta-alkylation of ketimine 1a

Entry

PG

Additive

Base

Solvent

T (ºC)

Yield (%)

1

PMP

Piv-Val-OH

K2CO3

1,4-dioxane

120

22

2

PMP

MesCO2H

K2CO3

1,4-dioxane

120

26

3

PMP

1-AdCO2H

K2CO3

1,4-dioxane

120

50

4

PMP

1-AdCO2H

K2CO3

1,4-dioxane

100

0

5

PMP

1-AdCO2H

K2CO3

1,4-dioxane

140

47

6

PMP

1-AdCO2H

K2CO3

NMP

120

0

7

PMP

1-AdCO2H

K2CO3

o-xylene

120

49

8

PMP

1-AdCO2H

K2CO3

DME

120

36

9

PMP

1-AdCO2H

K2CO3

PhMe

120

52

10

PMP

1-AdCO2H

Na2CO3

PhMe

120