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Scientific article
English

From Planar Chiral <i>o</i>-Chloro- and <i>o</i>-Iodo Benzaldehyde Tricarbonyl Chromium Complexes to Enantiopure Fused Hydroisoquinolines and Hydroquinolines

ContributorsRatni, Hasane; Crousse, Benoît; Kundig, Ernst Peter
Published inSynlett, no. 5, p. 626-628
Publication date1999
Abstract

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.

Keywords
  • Heck reaction
  • Aza-Diels-Alder reaction
  • Arene chromium complex
  • Planar chirality
  • Dihydroisoquinolines
Affiliation entities
Citation (ISO format)
RATNI, Hasane, CROUSSE, Benoît, KUNDIG, Ernst Peter. From Planar Chiral <i>o</i>-Chloro- and <i>o</i>-Iodo Benzaldehyde Tricarbonyl Chromium Complexes to Enantiopure Fused Hydroisoquinolines and Hydroquinolines. In: Synlett, 1999, n° 5, p. 626–628. doi: 10.1055/s-1999-2666
Identifiers
Journal ISSN0936-5214
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