. Author manuscript; available in PMC: 2011 Apr 16.

Published in final edited form as: Org Lett. 2010 Apr 16;12(8):1756–1759. doi: 10.1021/ol100365c

Table 3.

Enantioselective reduction of alkenyl and alkyl ketones.^a

entry	ketone	alcohol	catalyst	yield^b(%)	%ee^c
1	27	28	D	78	90
2	29	30	D	88	86
3	31	32	D	82	97
4	33	34	D	81	47
5	33	34	G	84	63
6	33	34	H	92	79
7	33	34	I	90	67
8	35	36	D	60	89
9	35	36	H^d	68	91

Reaction conditions: catalyst (10 mol %), catecholborane (1.6 equiv), 4 Å molecular sieves, toluene, −46 °C, 24 h.

Isolated yield.

Measured by chiral HPLC.

36 h.

graphic file with name nihms191219u5.jpg

entry	ketone	alcohol	catalyst	yield^b(%)	%ee^c
1	27	28	D	78	90
2	29	30	D	88	86
3	31	32	D	82	97
4	33	34	D	81	47
5	33	34	G	84	63
6	33	34	H	92	79
7	33	34	I	90	67
8	35	36	D	60	89
9	35	36	H^d	68	91

entry	ketone	alcohol	catalyst	yield^b(%)	%ee^c
1	27	28	D	78	90
2	29	30	D	88	86
3	31	32	D	82	97
4	33	34	D	81	47
5	33	34	G	84	63
6	33	34	H	92	79
7	33	34	I	90	67
8	35	36	D	60	89
9	35	36	H^d	68	91

entry	ketone	alcohol	catalyst	yield^b(%)	%ee^c
1	27	28	D	78	90
2	29	30	D	88	86
3	31	32	D	82	97
4	33	34	D	81	47
5	33	34	G	84	63
6	33	34	H	92	79
7	33	34	I	90	67
8	35	36	D	60	89
9	35	36	H^d	68	91