Skip to main content
. Author manuscript; available in PMC: 2009 Feb 10.
Published in final edited form as: J Am Chem Soc. 2007 Nov 17;129(49):15398–15404. doi: 10.1021/ja075204v

Table 1.

Asymmetric Allylboration of Acyl Iminesa

graphic file with name nihms62971f11.jpg
entry catalyst mol%b % yieldc erd
1 - - <5 -
2 7a 15 <5 50:50
3 7b 15 <5 55:45
4 7c 15 10 60:40
5 7d 15 51 50:50
6 7e 15 76 68:32
7 7f 15 81 93:7
8 7g 10 60 96.5:3.5
9 7h 15 85 96:4
10 7h 10 80 95:5
11 7h 5 60 90:10
12 7i 15 21 55:45
a

Reactions were run with 0.125 mmol borane, 0.125 mmol acyl imine, 15 mol % catalyst and in toluene (0.1 M) for 16 h under Ar, followed by flash chromatography on silica gel.

b

Catalyst concentration used relative to imine.

c

Isolated yield.

d

Enantiomeric ratios determined by chiral HPLC analysis.