Synlett 2015; 26(03): 323-326
DOI: 10.1055/s-0034-1379539
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© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Allylation of α-Amido Sulfones To Form Protected Homoallylic Amines

Jill A. Caputo
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA   Fax: +1(585)2760205   eMail: daniel.weix@rochester.edu
,
Marina Naodovic
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA   Fax: +1(585)2760205   eMail: daniel.weix@rochester.edu
,
Daniel J. Weix*
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA   Fax: +1(585)2760205   eMail: daniel.weix@rochester.edu
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Received: 02. September 2014

Accepted after revision: 21. Oktober 2014

Publikationsdatum:
07. Januar 2015 (online)


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Abstract

The allylation of stable, protected imine precursors, α-amido sulfones, with allylic acetates to form homoallylic amines is catalyzed by nickel under mild reducing conditions. Aliphatic and aryl imines are tolerated, as are substituted allylic acetates. In the case of substituted allylic acetates, high diastereoselectivity and regioselectivity is observed in some cases and the branched product is obtained almost exclusively.

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