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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 2.

Asymmetric Allylboration of Acyl Iminesa

graphic file with name nihms62971f12.jpg
entry solvent additive % yieldb erc
1 THF - 32 58:42
2 Et2O - 28 60:20
3 CH2Cl2 - 75 92:8
4 C6H5CH3: C6H5CF3 3:1 - 77 92:8
5 C6H5CH3 - 81 93:7
6 C6H5CH3 3Å MS 87 99:1
7 C6H5CH3 4Å MS 85 97:3
8 C6H5CH3 5Å MS 83 90:10
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

Isolated yield.

c

Enantiomeric ratios determined by chiral HPLC analysis.