Preparation of methoxy-substituted optically active 7-alkoxycarbonylcycloheptatrienes and their acid-promoted rearrangements

T Sugimura, M Kagawa, N Ohuchi, K Hagiya…

Index: Sugimura, Takashi; Kagawa, Masami; Ohuchi, Naoko; Hagiya, Kazutake; Okuyama, Tadashi Bulletin of the Chemical Society of Japan, 2005 , vol. 78, # 4 p. 671 - 676

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Citation Number: 4

Abstract

Four optically active cycloheptatriene derivatives carrying a methoxy group (s) at different positions were prepared by the 2, 4-pentanediol-tethered Büchner reaction. In addition to the high stereoselectivity, the tether also controlled the regioselectivity in a good-to-high degree. Some of the products are unstable under acidic conditions, resulting in isomerization through a prototropic reaction or aromatization. The Brønsted acid promoted ...