Chiral homoallylic and allylic sulfoxides as models for the stereochemical analysis of sulfoxide thiaoleates

F Daligault, A Arboré, C Nugier-Chauvin, H Patin

Index: Daligault, Franck; Arbore, Amelie; Nugier-Chauvin, Caroline; Patin, Henri Tetrahedron Asymmetry, 2004 , vol. 15, # 6 p. 917 - 924

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Citation Number: 12

Abstract

Both enantiomers of n-butyl allyl sulfoxide have been synthesized and are reported as models of bio-oxidized thiafatty acid analogues. The stereochemical analysis of these aliphatic sulfoxides as well as their homoallylic counterparts, were performed by the use of chiral NMR shift reagents. We first checked the validity of the chiral solvating NMR reagents method using the α-methoxyphenylacetic acid (MPA) and the Pirkle-like alcohol 1-(9- ...