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. 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 4.

Asymmetric Allylboration of Benzoyl Iminesa

graphic file with name nihms62971f14.jpg
entry R product % yieldb erc
1 CH3O 11a 13 57:43
2 t-BuO 11b 25 65:35
3 CH2=CHCH2O 11c 41 65:35
4 CH3 11d 52 70:30
5 p-(CH3)2N-C6H4 11e 76 97:3
6 p-CH3O-C6H4 11f 80 97.5:2.5
7 p-Br-C6H4 11g 83 96.5:3.5
8 p-F-C6H4 11h 84 97.5:2.5
9 p-NO2-C6H4 11i 92 99.5:0.5
10 o-F-C6H4 11j 83 69:31
11 (E)-PhCH=CH 11k 82 95:5
12 c-C6H11 11l 83 97:3
a

Reactions were run with 0.125 mmol borane, 0.125 mmol acyl imine, 15 mol % catalyst and 3Å molecular sieves in toluene (0.1 M) for 24 h under Ar, followed by flash chromatography on silica gel.

b

Isolated yield.

c

Enantiomeric ratios determined by chiral HPLC analysis.