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Synthesis 2006(8): 1333-1338
DOI: 10.1055/s-2006-926413
DOI: 10.1055/s-2006-926413
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Stereoselective Synthesis of (Z)-3-Aryl and Alkylmethylidene-1H-isoindolin-1-ones
Further Information
Received
14 October 2005
Publication Date:
28 March 2006 (online)
Publication History
Publication Date:
28 March 2006 (online)
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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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