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
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.
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HS, AD, AMD and QA thank CSIRO Australia for scholarships. We also thank Dr Roger Mulder, Dr Jo Cosgriff and Mr Carl Braybrook for assistance with collection and interpretation of NMR and/or MS data.