Asymmetric Synthesis of β-Hydroxy Sulfides Controlled by Remote Sulfoxides

Reactions of (S)-α-(methylthio)-2-(p-tolylsulfinyl)benzyl carbanion with different carbonyl compounds proceeds with complete control of the configuration at the benzylic position. Aldehydes yield easily separable mixtures of β-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselec...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-02, Vol.72 (3), p.1035-1038
Main Authors: Arroyo, Yolanda, Rodríguez, J. Félix, Santos, Mercedes, Sanz Tejedor, M. Ascensión, García Ruano, José Luis
Format: Article
Language:English
Subjects:
Benzene Derivatives - chemistry
Carbonates - chemistry
Chemistry
Exact sciences and technology
Models, Chemical
Organic chemistry
Stereoisomerism
Sulfhydryl Compounds - chemistry
Sulfides - chemical synthesis
Sulfonium Compounds - chemistry
Sulfoxides - chemistry
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Summary:Reactions of (S)-α-(methylthio)-2-(p-tolylsulfinyl)benzyl carbanion with different carbonyl compounds proceeds with complete control of the configuration at the benzylic position. Aldehydes yield easily separable mixtures of β-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselectivity depends on steric factors (from 20% to >98% de).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo062053q