A stereospecific synthesis of chiral cyclic sulfinamides.
Treatment of racemic or enantiomerically pure 2,1-benzothiazines (cyclic sulfoximines) with lithium triethylborohydride results in clean loss of the S-aryl group with complete retention of configuration at sulfur to produce diastereomerically and/or enantiomerically pure cyclic sulfinamides in excellent yield.
Harmata
Michael
M
Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA. harmatam@missouri.edu
Zheng
Pinguan
P
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013843:Thiazines / Q000737:chemistry
D000577:Amides; D013457:Sulfur Compounds; D013843:Thiazines; D001554:Benzene