Journal article

1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide

Hugo Santos, Amy Distiller, Asha M D'Souza, Quentin Arnoux, Jonathan M White, Adam G Meyer, John H Ryan

ORGANIC CHEMISTRY FRONTIERS | CHINESE CHEMICAL SOC | Published : 2015

Abstract

A series of phthalic anhydrides underwent a 1,3-dipolar cycloaddition reaction with N-benzylazomethine ylide, formed in situ from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine and a catalytic amount of trifluoroacetic acid, to produce unstable spiro(isobenzofuran-1,5′-oxazolidin)-3-ones. The spiro-fused oxazolidines were reduced with sodium borohydride to afford 1(3H)-isobenzofuranones, which were generally isolated in moderate to high overall yields.

University of Melbourne Researchers