ChemInform Abstract: Asymmetric Synthesis of Chiral Sulfoxides and Sulfinimines Using N- Sulfinylsultam.

✍ Scribed by W. OPPOLZER; O. FROELICH; C. WIAUX-ZAMAR; G. BERNARDINELLI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199732019

✦ Synopsis

The diastereomerically pure sulfinylating reagent (III) reacts with nucleophilic Grignard reagents or the zinc reagent derived from (VI) to yield chiral sulfoxides with excellent yields and enantioselectivities. Under specific conditions sequential reaction of (III) with LiN(Tms)2 followed by aldehydes (VIII) leads to enantiomerically pure sulfinimines. In all cases the chiral auxiliary ( I) is recovered quantitatively.

-(OPPOLZER, W.;