Tetrahedron

Catalytic and asymmetric [2, 3] sigmatropic rearrangement: Co (III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement

T Fukuda, R Irie, T Katsuki

文献索引：Fukuda, Tsutomu; Irie, Ryo; Katsuki, Tsutomu Tetrahedron, 1999 , vol. 55, # 3 p. 649 - 664

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被引用次数: 36

摘要

Reaction of allyl aryl sulfides and α-diazoacetic acid esters in the presence of optically active Co (III)-salen complex (8-Br) provided 3-substituted 2-arylthio-4-pentenoic acid esters stereoselectively by way of enantioselective S-ylide formation and subsequent diastereoselective [2, 3] sigmatropic rearrangement. For example, the reaction of cinnamyl phenyl sulfide and (−)-menthyl α-diazoacetate provided (−)-menthyl (2R, 3S)-2-phenylthio ...