Molecular Orbital Studies on Pericyclic Reactions of Cinnamyl Xanthates in. BETA.-Cyclodextrin Cavities.

M Eto, S Kubota, H Nakagawa, Y YOSHITAKE…

文献索引：Eto; Kubota; Nakagawa; Yoshitake; Harano Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 11 p. 1652 - 1659

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被引用次数: 7

摘要

The solid β-cyclodextrin (β-CyD) complex of O-cinnamyl S-methyl dithiocarbonates (xanthate, 1a), upon heating at 45° C, underwent asymmetric [3, 3]-sigmatropic rearrangement to give the optically S-(1-phenylallyl) S-methyl dithiocarbonate (2a) with 60% ee. Heating the β-CyD complex of 2a at 120° C caused extrusion of COS to give cinnamyl methyl sulfide (3a) in high yield. The reaction behavior and role of β-CyD are discussed ...