The Journal of Organic Chemistry

Conformational study of chiral alkenes: the influence of protective groups on the relative stability of ground-state rotational isomers

BW Gung, MA Wolf

Index: Gung, Benjamin W.; Wolf, Mark A. Journal of Organic Chemistry, 1993 , vol. 58, # 25 p. 7038 - 7044

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Citation Number: 32

Abstract

A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the groundstate (GS) conformations. If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes. Furthermore, conformer I becomes preferred even for the y-hydroxy-a, &unsaturated ...