Planar Chiral Tricarbonylchromium Complexes: Asymmetric Aza-Diels-Alder Reaction and Intramolecular Radical Cyclization to Indolizidines and Quinolizidines

Kundig, Ernst Peter; Xu, Long He; Romanens, Patrick; Bernardinelli, Gérald Hugues

doi:10.1055/s-1996-5385

Scientific article

English

Planar Chiral Tricarbonylchromium Complexes: Asymmetric Aza-Diels-Alder Reaction and Intramolecular Radical Cyclization to Indolizidines and Quinolizidines

ContributorsKundig, Ernst Peter; Xu, Long He; Romanens, Patrick; Bernardinelli, Gérald Hugues

Published inSynlett, no. 3, p. 270-272

Publication date1996

Abstract

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.

Keywords

Hetero Diels-Alder reaction
Planar chirality
Arene complex
Chromium radical cyclization

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

KUNDIG, Ernst Peter et al. Planar Chiral Tricarbonylchromium Complexes: Asymmetric Aza-Diels-Alder Reaction and Intramolecular Radical Cyclization to Indolizidines and Quinolizidines. In: Synlett, 1996, n° 3, p. 270–272. doi: 10.1055/s-1996-5385

Identifiers

PID : unige:6197
DOI : 10.1055/s-1996-5385

Journal ISSN0936-5214

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Planar Chiral Tricarbonylchromium Complexes: Asymmetric Aza-Diels-Alder Reaction and Intramolecular Radical Cyclization to Indolizidines and Quinolizidines

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