An Effective Deracemization of trans-1,2-Bis (phenylsulfenyl)cyclohexane

Abstract

A chiral S, S-donating C₂-symmetric ligand containing two stereogenic centers was prepared from rac-trans-1,2-cyclohexanediol. An effective deracemization of trans-1,2-bis(phenylsulfenyl)cyclohexane was achieved by the catalyzed enantioselective sulfoxidation, followed by the chromatographic separation of diastereomeric mono- and bis-sulfoxides. Subsequent recrystallization of enantiomerically enriched bissulfoxide and its final deoxygenation gave optically pure (1R,2R)-bis(phenylsulfenyl)cyclohexane.

Keywords:

• Chiral resolution
• chiral thioethers
• sulfoxidation

Dedicated to Professor Marian Mikołajczyk, CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

We are grateful to the Ministry of Science and Higher Education for financial support (Grant PBZ-KBN-126/T09/2004).