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Org Lett. 2014 Dec 19;16(24):6290-3. doi: 10.1021/ol502967x. Epub 2014 Dec 05.

Asymmetric synthesis of trisubstituted aziridines via aza-Darzens reaction of chiral sulfinimines.

Organic letters

Toni Moragas, Ian Churcher, William Lewis, Robert A Stockman

Affiliations

  1. School of Chemistry, University of Nottingham , Nottingham, NG7 2RD, U.K.

PMID: 25479333 DOI: 10.1021/ol502967x

Abstract

The aza-Darzens reaction of substituted 2-bromoesters with chiral tert-butane- and mesitylsulfinimines provides a rapid access to a range of highly substituted aziridines in good yields and excellent levels of stereoselectivity. The synthetic potential of this protocol is further enhanced by the successful removal of the sulfinyl motif, yielding simple access to chiral N-H aziridines in just three steps from commercial aldehyde precursors.

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