From Planar Chiral &lt;i&gt;o&lt;/i&gt;-Chloro- and &lt;i&gt;o&lt;/i&gt;-Iodo Benzaldehyde Tricarbonyl Chromium Complexes to Enantiopure Fused Hydroisoquinolines and Hydroquinolines

Ratni, Hasane; Crousse, Benoît; Kundig, Ernst Peter

doi:10.1055/s-1999-2666

Scientific article

English

From Planar Chiral o-Chloro- and o-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

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

Citation (ISO format)

RATNI, Hasane, CROUSSE, Benoît, KUNDIG, Ernst Peter. From Planar Chiral o-Chloro- and o-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

PID : unige:6199
DOI : 10.1055/s-1999-2666

Journal ISSN0936-5214

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

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

Technical informations