Synlett

A BF3-mediated nitrogen-to-carbon rearrangement of N-protected 2, 3-dihydro-3-hydroxy-1H-benzisoindol-1-ones, and its interception for a facile preparation of 3- …

AL Schwan, PA Duspara, MM Paquette, AR Merrill

Index: Schwan, Adrian L.; Duspara, Petar A.; Paquette, Michelle M.; Merrill, A. Rod Synlett, 2006 , # 18 p. 3115 - 3119

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Abstract

Abstract A BF 3-mediated release of the hydroxy and the nitrogen-protecting group of N- (cumyl or 1, 1-diphenylethyl)-2, 3-dihydro-3-hydroxy-1H-benzisoindol-1-ones is accompanied by recombination of the nitrogen-protecting unit to the 3-position of the ring system. The addition of sulfur or carbon nucleophiles affords products of preferential capture of the rearrangement intermediate offering a convenient and rapid synthetic route to N- ...