Tetrahedron Letters

Highly stereocontrolled synthesis of (2e, 4z)-dienic esters by alumina catalyst

S Tsuboi, T Masuda, H Makino, A Takeda

Index: Tsuboi, Sadao; Masuda, Toshihide; Makino, Hiroshi; Takeda, Akira Tetrahedron Letters, 1982 , vol. 23, # 2 p. 209 - 212

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Citation Number: 16

Abstract

Summary: Thermal treatment of p-allenic esters(2) with alumina catalyst in aprotic solvents yielded(2E, &Z)-dienoic esters(3) in 57-87s yields with 91-100% stereoselectivity. p-Allenic esters 2, which are readily obtained from trialkyl orthoacetate and propargylic alcohols(I.)', can be converted to 2, 4-dienoic esters by the prototropic rearrangement with basic or acidic catalysts. 394 However, these procedures hitherto reported are not satisfactory in the ...