Enantioselective Routes to Sulfoxides Based upon Carbon-for-Carbon Substitution Reactions on the Sulfinyl Group

Abstract

Grignard reagents were found to displace carbanionic leaving groups from suitable sulfinyl compounds. Because the process occurred with full inversion at the sulfinyl group, it was possible to set up an easy and straightforward route to chiral nonracemic sulfoxides. The starting compounds were easily produced, mainly by enantioselective oxidation of prochiral sulfides, and then the carbon-for-carbon displacement was effected with formation of a variety of new enantiopure sulfoxides.

keywords:

• Carbanions;
• Grignard reagents;
• leaving groups;
• sulfoxides

Acknowledgments

This work was financially supported in part by the Ministero dell'Istruzione, dell Università e della Ricerca, Rome (National Project “Stereoselezione in Sintesi Organica. Metodologie e Applicazioni”), by the University of Bari and by the Fondo per gli Investimenti della Ricezla di Base (FIRB) project “Progettazione, preparazione e valutazione biologica e farmacologica di nuove molecole organiche quali potenziali farmaci innovativi.”