Synthesis of Aza-, Oxa-, and Thiabicyclo [3.1. 0] hexane Heterocycles from a Common Synthetic Intermediate

…, P Jaishankar, R Venkatachalam, MF Gordeev

Index: Renslo, Adam R.; Gao, Hongwu; Jaishankar, Priyadarshini; Venkatachalam, Revathy; Gordeev, Mikhail F. Organic Letters, 2005 , vol. 7, # 13 p. 2627 - 2630

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Citation Number: 15

Abstract

An efficient and stereospecific approach to the synthesis of structurally constrained aza-, oxa- , and thiabicyclo [3.1. 0] hexane heterocycles has been achieved through application of the intramolecular cyclopropanation reaction of diazoacetates. The various constrained heterocycles (X= N, O, or S) are conveniently prepared from a common diol intermediate accessible from readily available cinnamyl alcohols. Application of the methodology to the ...