Stereoselective synthesis of substituted dienes by the double ortho ester Claisen rearrangement

S Hong, S Yoon, B Yu

Index: Hong, Suk-Pyo; Yoon, Sung-Jun; Yu, Byung-Chan Tetrahedron Letters, 2005 , vol. 46, # 5 p. 779 - 782

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Citation Number: 5

Abstract

This letter shows the highly stereoselective synthesis of substituted (E)-1, 3-dienes from substituted propargylic diols via the double ortho ester Claisen rearrangement. The cyclohexyl-substituted diene undergoes thermal Diels–Alder cycloaddition with maleic anhydride to produce the corresponding bicyclic diester in highly stereoselective manner.