Dependence of ring closure stereoselectivity on the nature of the leaving group: application to the synthesis of a new class of chiral sulfoxide for the control of asymmetric aldol reactions
Abstract
Enantiomerically pure cyclic sulfinamide (S(s)R)-(+)-1 [(S)-cis-1], which has application to the control of asymmetric aldol reactions via a derived sulfoxide, has been prepared in diastereoisomerically pure form from the sulfinic acid (R)-(–)-5 using thionyl chloride-4-dimethylaminopyridine (DMAP); replacement of DMAP with pyridine or triethylamine gave both diastereoisomers of 1 in low diastereoisomeric excess.
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