Tetrahedron letters

Selective synthesis of γ, δ-unsaturated carboxylic acid derivatives by the Ni (CO) 4-induced ring-opening carbonylation reaction

T Hirao, S Nagata, T Agawa

Index: Hirao, Toshikazu; Nagata, Shinichiro; Agawa, Toshio Tetrahedron Letters, 1985 , vol. 26, # 47 p. 5795 - 5798

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Citation Number: 14

Abstract

Abstract gem-Dibromocyclopropanes bearing the chloromethyl or mesyloxymethyl substituent at the vicinal position underwent the Ni (CO) 4-induced ring-opening carbonylation reaction with alcohol or amines leading to the γ, δ-unsaturated carboxylic acid derivatives selectively via nickel enolate intermediates. Successful utilization of N, N- dimethyltrimethylsilylamine as an initial nucleophile resulted in condensation with ...