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

MC Carreno, JL Garcia Ruano…

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

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被引用次数: 36

摘要

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 ...