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Synlett 1996; 1996(3): 270-272
DOI: 10.1055/s-1996-5385
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Planar Chiral Tricarbonylchromium Complexes: Asymmetric Aza-Diels-Alder Reaction and Intramolecular Radical Cyclization to Indolizines and Quinolizidines

E. Peter Kündig* , Long He Xu, Patrick Romanens, Gérald Bernardinelli
  • *Département de Chimie Organique, Université de Genève, 30 quai Ernest Ansermet, CH-1211 Genève 4, Switzerland, Fax (+41 22) 328 7396; e-mail: Peter.Kundig@chiorg.unige.ch
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Publication Date:
31 December 2000 (online)

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Highly diastereoselective Lewis acid mediated aza-Diels-Alder reactions of planar chiral Cr(CO)3 complexes of o-substituted benzaldehyde imines are reported. Enantio- and diastereopure complexes of 2-aryl-2,3-dihydro-4-pyridinones obtained via this route undergo intramolecular radical cyclization to the title compounds with complete diastereoselectivity.

hetero Diels-Alder reaction - planar chirality - arene complex - chromium radical cyclization