Synthesis and Ring??Opening Reactions of the Diastereoisomeric cis??and trans??Epoxides Derived from 3??(Benzyloxy) cyclopentene and 2??(Benzyloxy)??2, 5?? …

…, V Di Bussolo, L Favero, F Macchia…

Index: Crotti, Paolo; Bussolo, Valeria Di; Favero, Lucilla; Macchia, Franco; Pineschi, Mauro European Journal of Organic Chemistry, 1998 , # 8 p. 1675 - 1686

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Citation Number: 22

Abstract

Abstract The regiochemical outcome of the ring-opening of epoxides bearing remote polar functionalities has been established in the case of carbocyclic (1 and 2) and the corresponding furanosidic (3 and 4) title epoxides. Under standard conditions, the regioisomeric C-1 products are the sole (from trans epoxides 2 and 4) or predominant (from cis epoxides 1 and 3) ring-opening products. However, under chelating conditions, and ...

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