Synthesis 2003(13): 2110-2114
DOI: 10.1055/s-2003-41453
PSP
© Georg Thieme Verlag Stuttgart · New York

The Diastereoselective Barbier-Type Addition to Chiral N-Tosylimines

Anna Kuleszaa, Janusz Jurczak*a,b
a Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw
b Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw
Fax: +48(22)8225996; e-Mail: [email protected];
Further Information

Publication History

Received 28 November 2002
Publication Date:
10 September 2003 (online)

Abstract

The Barbier approach was used for diastereoselective formation of allylamino acid derivatives. The stereochemical models for nucleophilic addition to N-tosylimines bearing various chiral auxiliaries such as (2R)-bornano-10,2-sultam, (R)-8-phenylmenthol, and 10-N,N-dicyclohexylsulfamoyl-(R)-isoborneol are proposed.

    References

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The crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-194392. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK [fax (+44)1223336033; e-mail: [email protected]].