The intramolecular, stereoselective addition of sulfoximine carbanions to alpha,beta-unsaturated esters.
ortho-Bromocinnamates can be coupled with methyl phenylsulfoximine to afford N-arylsulfoximines in excellent yield. Treatment of these products with an amide base results in a completely stereoselective cyclization to afford enantiomerically pure benzothiazines. This reaction is stereospecific.
Harmata
Michael
M
Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA. harmatam@missouri.edu
Hong
Xuechuan
X
D002934:Cinnamates / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000138:chemical synthesis / Q000737:chemistry*
D002934:Cinnamates; D004952:Esters; D007097:Imines; D013454:Sulfoxides