A Stereoselective Synthesis of (Z)-3-Aryl and Alkylmethylidene-1H-isoindolin-1-ones

Marc Lamblin; Axel Couture; Eric Deniau; Pierre Grandclaudon

doi:10.1055/s-2006-926413

PAPER

A Stereoselective Synthesis of (Z)-3-Aryl and Alkylmethylidene-1H-isoindolin-1-ones

Marc Lamblin, Axel Couture*, Eric Deniau, Pierre Grandclaudon
UMR 8009 ‘Chimie Organique et Macromoléculaire’, Laboratoire de Chimie Organique Physique, Université des Sciences et Technologies de Lille, Bâtiment C3(2), 59655 Villeneuve d"Ascq cedex, France
Fax: +33(320)336309; e-Mail: axel.couture@univ-lille1.fr;

Abstract

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Abstract

A series of Z-configured (hetero)aryl and alkylmethylideneisoindolin-1-ones has been efficiently prepared by treatment of N-methoxycarbonylisoindolin-1-ones with a base and reaction with selected aldehydes. The parent N-acylated isoindolin-1-ones have been assembled by a Parham-type cyclization of N-(2-iodoarylmethyl)dicarbamates.

Key words

carbanions - Mitsonobu reaction - cyclizations - olefination - stereoselectivity

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References

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