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Asymmetric photoinduced electrocyclic ring closure of chiral aromatic enehydrazides. Application to the asymmetric synthesis of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines.
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1  Unité de Catalyse et de Chimie du Solide (UCCS) UMR CNRS 8181 - Axe CCM - Equipe CASECO


A flexible route for the stereoselective synthesis of a variety of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines has been developed. The key step is a diastereoselective photoinduced 6π-electrocyclic ring closure of enantiopure aromatic enehydrazides via a 1,4-remote asymmetric induction. N-N bond cleavage to release the chiral appendage from the preliminary annulated compounds and/or concomitant reduction of the lactam carbonyl group completed the synthesis of the title compounds.

Keywords: Asymmetric synthesis, enol phosphates, cross-coupling, chiral enehydrazides, photocyclization, 3-arylisoquinolones