Asymmetric Synthesis of Trisubstituted Aziridines via Aza-Darzens Reaction of Chiral Sulfinimines

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 su...

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Bibliographic Details
Published in:Organic letters 2014-12, Vol.16 (24), p.6290-6293
Main Authors: Moragas, Toni, Churcher, Ian, Lewis, William, Stockman, Robert A.
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502967x