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

In situ-generated ortho-halogenated phenylmeth-animines coordinated to the tnicarbonylchromium 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.