Synthesis of Enantiopure Aminocyclopropanes by Diastereoselective Addition of a Chiral Amino Substituted Organozinc Carbenoid to Alkenes

Guillaume Bégis; Tom D. Sheppard; David E. Cladingboel; William B. Motherwell; Derek A. Tocher

doi:10.1055/s-2005-918469

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Synthesis 2005(19): 3186-3188
DOI: 10.1055/s-2005-918469

SHORTPAPER

Synthesis of Enantiopure Aminocyclopropanes by Diastereoselective Addition of a Chiral Amino Substituted Organozinc Carbenoid to Alkenes

Guillaume Bégis^a, Tom D. Sheppard^a, David E. Cladingboel^b, William B. Motherwell*^a, Derek A. Tocher^a
^a Department of Chemistry, Christopher Ingold Laboratories, University College London, 20 Gordon Street, London, WC1H 0AJ, UK
^b AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, LE11 5RH, UK
Fax: +44(20)76797524; e-Mail: w.b.motherwell@ucl.ac.uk;

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Publication History

Received 6 September 2005
Publication Date:
14 November 2005 (online)

Abstract
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Abstract

The synthesis of enantiopure aminocyclopropanes is reported, via direct aminocyclopropanation of alkenes with a zinc carbenoid containing a chiral auxiliary. The methodology was applied to the synthesis of a protected aminocyclopropane present in the immunosuppressant Belactosin A.

Key words

alkenes - carbenoids - chiral auxiliaries - electrophilic addition - zinc

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