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Synlett 1998; 1998(4): 367-368
DOI: 10.1055/s-1998-1681
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Preparation of Both Diastereomers of Homoallylic Amines by Allylmetalation of Methyl N-Benzylidene-(S)-valinate

Ashraf A. El-Shehawy* , Mahmoud A. Omara, Koichi Ito, Shinichi Itsuno
  • *Department of Materials Science, Toyohashi University of Technology, Toyohashi 441-8580, Japan; Fax + 81(532)44 68 13; E-mail: itsuno@tutms.tu.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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The reaction of enantiopure imine 1 with methallyl or prenylzinc reagents affords homoallylic amines having (S,S) configuration with up to 100% diastereomeric excess. Another diastereomer, (R,S)-amines, is obtained from the same imine 1 by using allylboron reagents.

homoallylamine - methylvalinate - triallylborane - allylzinc reagents