Remarkably Mild and Simple Preparation of Sulfenate Anions from β-Sulfinylesters:  A New Route to Enantioenriched Sulfoxides

Remarkably Mild and Simple Preparation of Sulfenate Anions from β-Sulfinylesters:  A New Route to Enantioenriched Sulfoxides

A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using β-sulfinylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulf...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 70; no. 7; pp. 2812 - 2815
Main Authors: Caupène, Caroline, Boudou, Cédric, Perrio, Stéphane, Metzner, Patrick
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 01-04-2005
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Michael addition
Solvent effect
Anions
Sulfenate
Sulfoxide
Sparteine
Chemical synthesis
Alkylation
Organic halogen compounds
Low temperature
Deprotonation
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Summary:A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using β-sulfinylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulfenates are subsequently converted into sulfoxides in good to excellent yield. Extension of the methodology to an unprecedented access to nonracemic sulfoxides by introduction of an enantiopure ligand, (−)-sparteine, is also described.
Bibliography:istex:4B2F084542B2A07DD7510CE75BE3533015EFEAB7
ark:/67375/TPS-CJBKBJCB-R
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0478003