Journal of the American Chemical Society

Stereochemistry of allyl sulfones. On the structure of metalated allyl sulfones and their stereochemistry of alkylation

BM Trost, NR Schmuff

Index: Trost,B.M.; Schmuff,N.R. Journal of the American Chemical Society, 1985 , vol. 107, p. 396

Full Text: HTML

Citation Number: 80

Abstract

Abstract: Stereochemical studies involving alkylation of metalated allyl sulfones are probed to address the question of the structure of these important synthetic intermediates. In contrast to recent conclusions, both experimental and theoretical, declaring sulfone-stabilized carbanions planar, the diastereoselectivity of these alkylations questions such conclusions even though the additional allylic conjugation would have been anticipated to provide a ...