Table 1 Optimization of reaction conditionsa

From: Dinickel-catalyzed enantioselective reductive addition of imines with vinyl halides

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Entry

L

X

Yield (%)

e.r.

1b,c

L1

5

61

98:2

2b,c

L2

5

61

93:7

3b,c

L3

5

53

93:7

4c

L1

5

79

98:2

5c,d

L1

5

42

95:5

6

L1

5

91

98:2

7e

L1

5

54

98:2

8

L4

10

trace

9

L5

10

trace

10

L6

10

trace

11

L7

10

28

50:50

12

L8

10

13

53:47

13

L9

10

28

62:38

14

L10

10

55

62:38

  1. aUnless noted, imine 1a (0.2 mmol), styrenyl chloride 2a (1.5 equiv), NiBr2•glyme (10 mol%), L (x mol%), NaI (2.0 equiv) and Zn (2.0 equiv) were stirred in THF (0.2 M) at 25 °C for 48 h, isolated yield.
  2. bReaction with 2a (1.2 equiv) for 24 h.
  3. c0.1 mmol scale in THF (0.1 M).
  4. dMn was used instead of Zn.
  5. eWithout NaI.