Synlett 2004(4): 711-713  
DOI: 10.1055/s-2004-817743
LETTER
© Georg Thieme Verlag Stuttgart · New York

Unexpected Temperature, Time and Solvent Effects in the Catalytic ­Asymmetric aza-Diels-Alder Reaction of an Ethyl Glyoxylate-derived N-Aryl Imine with Danishefsky’s Diene Catalysed by a BINOL-Zinc Complex

Stéphane Guillarme, Andrew Whiting*
Department of Chemistry, Science Laboratories, University of Durham, South Road, Durham, DH1 3LE, UK
Fax: 44 (0) 191 384 3747.; e-Mail: andy.whiting@durham.ac.uk.;
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Publikationsverlauf

Received 27 November 2003
Publikationsdatum:
29. Januar 2004 (online)

Abstract:

The catalytic asymmetric aza-Diels-Alder reaction of an ethyl glyoxylate-derived N-aryl imine with Danishefsky’s diene using a BINOL-zinc complex provides the corresponding cycloadduct with moderate to high enantioselectivity, depending on the solvent, temperature and reaction time.