Tetrahedron

Cyclohexenol annulation via the alkoxy-accelerated rearrangement of vinylcyclobutanes

RL Danheiser, C Martinez-Davila, H Sard

Index: Danheiser, Rick L.; Martinez-Davila, Carlos; Sard, Howard Tetrahedron, 1981 , vol. 37, # 23 p. 3943 - 3950

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Citation Number: 71

Abstract

The lithium and potassium salts of 2-vinylcyclobutanols undergo vinylcyclobutane rearrangement at 25–70°, providing an efficient method for the synthesis of 3-cyclohexenol derivatives. 2-Vinylcyclobutanones are prepared from α, β-unsaturated carbonyl compounds by the method of Trost and via [2+ 2]-cycloadditions of olefins and vinylketenes. Addition of hydride or alkyllithium reagents then generates 2-vinylcyclobutanol salts which directly ...