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Synlett 1999; 1999(5): 626-628
DOI: 10.1055/s-1999-2666
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From Planar Chiral o-Chloro and o-Iodo Benzaldehyde Tricarbonyl Chromium Complexes to Enantiopure Fused Hydroisoquinolines and Hydroquinolines

Hassen Ratni* , Benoît Crousse, E. Peter Kündig
  • *Département de Chimie Organique, Université de Genève, 30 Quai Ernest Ansermet, CH-1211 Genève 4, Switzerland; Fax +41(22)32 873 96; E-mail: Peter.Kundig@chiorg.unige.ch
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Publication Date:
31 December 1999 (online)

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In situ-generated ortho-halogenated phenylmeth-animines coordinated to the tricarbonylchromium group undergo highly diastereoselective sequential aza-Diels-Alder/intramolecular Heck cyclization reactions to yield enantiopure hydroisoquinolines. Diastereoselective allylation at C(5) of the intermediate 6-aryl dihydropyridone complex followed by intramolecular Heck reaction affords hydroquinoline products.

Heck reaction - aza-Diels-Alder reaction - arene chromium complex - planar chirality - dihydroisoquinolines

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