Tetrahedron Letters

Synthesis and asymmetric Diels-Alder reactions of (S)-2-p-tolylsulfinyl-1, 4-benzoquinone

MC Carreño, JLG Ruano, A Urbano

文献索引：Carreno, M. Carmen; Ruano, Jose L. Garcia; Urbano, Antonio Tetrahedron Letters, 1989 , vol. 30, # 30 p. 4003 - 4006

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被引用次数: 56

摘要

Abstract Optically pure (S)-2-p-tolylsulfinyl-1, 4-benzoquinone (5) is readily obtained by deketalization of the corresponding quinone bisketal 4, synthesized by Andersen's type synthesis on 2-bromo-1, 4-dimethoxybenzene (1) followed by anodic oxidation of the resulting sulfoxide. The Diels-Alder reaction of cyclopentadiene with 5 took place on C 5-C 6 dienophilic double bond showing high facial selectivity, which can be inverted by using ...