Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1, 4-naphthoquinones

MC Carreno, JL Garcia Ruano…

Index: Carreno, M. Carmen; Ruano, Jose L. Garcia; Urbano, Antonio Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6870 - 6876

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Citation Number: 36

Abstract

The asymmetric Diels-Alder reactions of (S)-2-@-tolylsulfiiyl)-1, 4-naphthoquinones la-with cyclic dienes have been explored. The high T facial diastereoselectivity observed can be reversed in the presence of ZnBrz. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfiiyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral la-c offers a convenient ...

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