Tetrahedron letters

Access to diversely α-substituted cyclopentenones from α-chlorocyclopentenones

A Giannini, Y Coquerel, AE Greene, JP Deprés

Index: Giannini, Audrey; Coquerel, Yoann; Greene, Andrew E.; Depres, Jean-Pierre Tetrahedron Letters, 2004 , vol. 45, # 36 p. 6749 - 6751

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Citation Number: 4

Abstract

The development of effective new approaches to substituted cyclopentenones constitutes a worthwhile synthetic pursuit because of their ubiquitousness in nature and their usefulness as synthetic building blocks. The sequence developed several years ago in our laboratory, consisting of regio- and stereoselective [2 + 2] cycloaddition of dichloroketene with olefins, followed by diazomethane ring expansion and dehydrochlorination, leads efficiently to α-chlorocyclopentenones ( ...