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Synlett 1999; 1999(5): 626-628
DOI: 10.1055/s-1999-2666
DOI: 10.1055/s-1999-2666
letter
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From Planar Chiral o-Chloro and o-Iodo Benzaldehyde Tricarbonyl Chromium Complexes to Enantiopure Fused Hydroisoquinolines and Hydroquinolines
Further Information
Publication History
Publication Date:
31 December 1999 (online)
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