Download PDF
Synlett 1998; 1998(4): 367-368
DOI: 10.1055/s-1998-1681
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >