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

Abstract

1997 stereochemistry stereochemistry (general, optical resolution) O 0030 -019Asymmetric Synthesis of Chiral Sulfoxides and Sulfinimines Using N-Sulfinylsultam.-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.; FROELICH, O.; WIAUX-ZAMAR, C.; BERNARDINELLI, G.; Tetrahedron Lett. 38 (1997Lett. 38 ( ) 16, 2825Lett. 38 ( -2828 Dep. Chim. Org., Univ. Geneve, CH-1211 Geneve, Switz.; EN)