Chiral Sulfilimines Through Rhodium Catalysis

Significance

In previous work the authors have used sulfonimidamides to generate chiral nitrenes and subsequently applied them to metal-catalyzed insertion into C=C and C-H bonds (J. Am. Chem. Soc. 2008, 130, 343). They have applied this methodology to diastereoselective ­iminaton of sulfides using a chiral nitrene. The present method tolerates a broad range of sulfides to give sulfilimines in high yields and modest to good de values. Oxidation of the product with MCPBA conveniently affords the corresponding sulfoximine.