Enantioselective Synthesis of Benzyl tert-Butyl Sulfoxides

✍ Scribed by Majid Khalil Syed; Mike Casey

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 381 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201101059

✦ Synopsis

Abstract

Enantiomerically pure benzyl sulfoxides are effective tools for the formation of new C–C bonds with control of configuration at new stereogenic centres. The reaction of enantioenriched tert‐butyl tert‐butanethiosulfinate with benzyllithium derivatives, obtained by deprotonation of the corresponding toluene derivatives, gave a wide variety of benzyl tert‐butyl sulfoxides with complete inversion of configuration. The benzyl sulfoxides were deprotonated in situ, and addition of the electrophiles gave α‐substituted products with good diastereoselectivity.