Synlett 2015; 26(03): 355-358
DOI: 10.1055/s-0034-1379735
letter
© Georg Thieme Verlag Stuttgart · New York

Proline-Catalyzed α-Aminooxylation of β-Amino Aldehydes: Access to Enantiomerically Pure syn- and anti-3-Amino-3-aryl-1,2-alkanediols

V. Venkataramasubramanian
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, India   Email: a.sudalai@ncl.res.in
,
I. N. Chaithanya Kiran
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, India   Email: a.sudalai@ncl.res.in
,
Arumugam Sudalai*
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, India   Email: a.sudalai@ncl.res.in
› Author Affiliations
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Publication History

Received: 13 October 2014

Accepted after revision: 18 November 2014

Publication Date:
09 January 2015 (online)


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Abstract

A new synthetic method for enantioselective synthesis of syn or anti-3-amino-3-aryl-1,2-alkanediols via proline catalyzed α-aminooxylation of β-amino aldehydes are described. This methodology is successfully applied to a concise and protecting group-free asymmetric synthesis of (–)-cytoxazone, (+)-epi-cytoxazone and formal synthesis of N-thiolated 2-oxazolidinone.

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