Asymmetric synthesis of beta-hydroxy sulfides controlled by remote sulfoxides

Yolanda Arroyo; J Félix Rodríguez; Mercedes Santos; M Ascensión Sanz Tejedor; José Luis García Ruano

doi:10.1021/jo062053q

Asymmetric synthesis of beta-hydroxy sulfides controlled by remote sulfoxides

J Org Chem. 2007 Feb 2;72(3):1035-8. doi: 10.1021/jo062053q.

Authors

Yolanda Arroyo¹, J Félix Rodríguez, Mercedes Santos, M Ascensión Sanz Tejedor, José Luis García Ruano

Affiliation

¹ Departamento de Química OrgAnica (ETSII), Universidad de Valladolid, Paseo del Cauce s/n, 47011 Valladolid, Spain.

PMID: 17253831
DOI: 10.1021/jo062053q

Abstract

Reactions of (S)-alpha-(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 beta-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselectivity depends on steric factors (from 20% to >98% de).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / chemistry
Carbonates / chemistry
Models, Chemical
Stereoisomerism
Sulfhydryl Compounds / chemistry
Sulfides / chemical synthesis*
Sulfonium Compounds / chemistry
Sulfoxides / chemistry*

Substances

Benzene Derivatives
Carbonates
Sulfhydryl Compounds
Sulfides
Sulfonium Compounds
Sulfoxides