Electrophile-initiated ring-opening reactions of 2-methylene-6, 6-dimethylbicyclo [3.1. 0] hexanes. New methodology for the synthesis of highly functionalized 1, 2, 3- …

RA Roberts, V Schuell, LA Paquette

Index: Roberts, Richard A.; Schuell, Volker; Paquette, Leo A. Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 2076 - 2084

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Citation Number: 27

Abstract

A pair of 1-substituted 2-methylene-6, 6-dimethylbicyclo [3.1. O] hexanes has been determined to undergo smooth cyclopropane ring opening with formation of 1, 2, 3- trisubstituted cyclopentenes in the presence of electrophilic or free radical agents. High optical purity can be incorporated into these products, starting with the readily available Z- menthyl6, 6-dimethyl-2-oxobicyclo [3. l. 0] hexanel-carboxylate, the two diastereomers of ...