Tetrahedron

A facile method for synthesis of three carbon-homologated carboxylic acid by regioselective ring-opening of β-propiolactones with organocopper reagents

M Kawashima, T Sato, T Fujisawa

Index: Kawashima, Masatoshi; Sato, Toshio; Fujisawa, Tamotsu Tetrahedron, 1989 , vol. 45, # 2 p. 403 - 412

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Citation Number: 44

Abstract

Organocopper reagents, such as diorganocuprates, organocopper-tributylphosphine, and Grignard reagents in the presence of a copper (I) salt, reacted with β-propiolactones by regioselectlve β-carbon-oxygen fission to give 3-substituted propionic acids. Among these three kinds of organocopper reagents, diorganocuprate, especially halomagnesium cuprate gave the highest yields of the acids, which was remarkably observed in the ring-opening ...