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Type: Artigo de periódico
Title: Diastereofacial selectivity in ketene [2+2] cycloaddition to endocyclic enecarbamates bearing a chiral auxiliary. Synthesis of the (-)-Geissman-Waiss lactone
Author: Miranda, PCML
Correia, CRD
Abstract: The diastereofacial selectivity of enecarbamates bearing a chiral auxiliary was evaluated for the [2+2]cycloaddition with dichloroketenes. Diastereofacial selectivity ranged from zero (bornyl and menthyl) to 60% (Greene's auxiliary and 8-phenylmenthyl). Chromatography separation of the diastereomeric azacyclobutanones derived from the 8-phenylmenthyl enecarbamate permitted an enantiodivergent synthesis of the (-)-Geissman-Waiss lactone, a key intermediate in the synthesis of necine bases. (C) 1999 Elsevier Science Ltd. All rights reserved.
Subject: chiral auxiliaries
Geissman-Waiss lactone
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron Letters. Pergamon-elsevier Science Ltd, v. 40, n. 44, n. 7735, n. 7738, 1999.
Rights: fechado
Identifier DOI: 10.1016/S0040-4039(99)01638-X
Date Issue: 1999
Appears in Collections:Unicamp - Artigos e Outros Documentos

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