Table 1 Reaction condition optimizationaView full size image

From: Asymmetric dihydroboration of allenes enabled by ligand relay catalysis

Entry

[Co]

L

L*

Solvent

Yieldb

Eec

1

Co(acac)2

tpy

L*1

MTBE

40%

82%

2

Co(acac)2

tpy

L*2

MTBE

45%

80%

3

Co(acac)2

tpy

L*3

MTBE

52%

93%

4

Co(acac)2

tpy

L*4

MTBE

79%

95%

5d

Co(acac)2

tpy

L*4

MTBE

82%

94%

6

Co(acac)2

tpy

L*5

MTBE

ND

7

Co(acac)2

L1

L*4

MTBE

42%

94%

8

Co(acac)2

L2

L*4

MTBE

11%

70%

9

Co(acac)2

bpy

L*4

MTBE

ND

10

Co(acac)3

tpy

L*4

MTBE

14%

59%

11

Co(OAc)2

tpy

L*4

MTBE

21%

89%

12

Co(acac)2

tpy

L*4

Et2O

76%

88%

13

Co(acac)2

tpy

L*4

THF

27%

79%

14

Co(acac)2

tpy

L*4

Hexane

20%

29%

View full size image

  1. aReaction conditions: 1a (0.2 mmol), [Co] (10 mol%), L (5 mol%), L* (5 mol%), HBpin (3.5 equiv), solvent (1.0 mL), 30 °C, 30 h; then THF (0.1 M), H2O2 (30%, 0.4 mL), NaOH (3 M, 0.4 mL). bIsolated yield. cEe was determined by HPLC on a chiral stationary phase. dReaction was run for 39 h.