Diastereoselective Intramolecular meta Photocycloaddition of Side??Chain??Substituted 5??(2??Methoxyphenyl) pent??1??enes

…, MP Wamelink, G Lodder, J Cornelisse

Index: Timmermans, Johan L.; Wamelink, Marc P.; Lodder, Gerrit; Cornelisse, Jan European Journal of Organic Chemistry, 1999 , # 2 p. 463 - 470

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Citation Number: 14

Abstract

Abstract Irradiation of a series of 5-(2-methoxyphenyl) pent-1-enes substituted with a hydroxy or trimethylsilyloxy group at the α-, β-, or γ-position of the side-chain yields in all cases meta photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that the diastereoselectivity originates from minimization of steric interactions between the side-chain substituent and the ortho-methoxy group at the arene ...