Table 1 Optimization of reaction conditionsa.

From: Non-enzymatic catalytic asymmetric cyanation of acylsilanes

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Entry

Catalyst (mol%)

Solvent

Yield (%)b

ee (%)

1

3a (20)

CHCl3

88

94

2

3b (20)

CHCl3

42

83

3

3c (20)

CHCl3

22

49

4

3d (20)

CHCl3

31

–61

5

3e (20)

CHCl3

23

19

6

3f (20)

CHCl3

24

41

7

3g (20)

CHCl3

<5

—

8c

3h (20)

CHCl3

93

21

9

3a (20)

CH2Cl2

84

94

10

3a (20)

EtOAc

61

95

11

3a (20)

acetone

57

95

12

3a (20)

THF

39

89

13

3a (20)

toluene

48

93

14

3a (20)

hexane

15

60

15

3a (10)

CHCl3

37

95

16d

3a (10)

CHCl3

36

96

  1. aReactions were run using 1a (0.20 mmol), TMSCN (0.40 mmol), and the catalyst in the solvent (0.20 mL).
  2. bIsolated yields.
  3. cThe trimethylsilyl ether of 2a was obtained as the product.
  4. dReaction was run for 48 h.
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