Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones

José L. García Ruano, David Barros, M. Carmen Maestro, Ana M. Martín Castro, Paul R. Raithby

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

We describe the addition reactions of α-thiocarbanions derived from sulfoxides, thioethers, and sulfones to 2-(p-tolylsulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the substrate, but it is modulated by the nature of the sulfur function at the reagent (SOTol>SO2Ph>SPh). The highly stereoselective formation of the second stereogenic center generated in these reactions from prochiral anions is only achieved with sulfinylcarbanions, the configuration of which controls that of such a center. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4385-4395
Number of pages11
JournalTetrahedron Asymmetry
Volume11
Issue number21
DOIs
Publication statusPublished - 3 Nov 2000

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones'. Together they form a unique fingerprint.

Cite this