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Sulfinylimidates as chiral amide equivalents for irreversible, asymmetric aldol reactions.

Authors
  • Bartrum, Hannah E
  • Viceriat, Audrey
  • Carret, Sébastien
  • Poisson, Jean-François
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Apr 04, 2014
Volume
16
Issue
7
Pages
1972–1975
Identifiers
DOI: 10.1021/ol500520h
PMID: 24646321
Source
Medline
License
Unknown

Abstract

A highly selective N-sulfinylimidate aldolization has been developed under mildly basic conditions leading to diastereopure products of high synthetic potential. The innate reversibility of this aldolization was suppressed by the use of titanium as the Lewis acid. An application of this methodology via the synthesis of a potential neurotransmitter reuptake inhibitor is illustrated.

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