Asymmetric photoinduced electrocyclic ring closure of chiral aromatic enehydrazides. Application to the asymmetric synthesis of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines.

Eric DENIAU; Stéphane LEBRUN

doi:10.3390/ecsoc-19-a031

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Asymmetric photoinduced electrocyclic ring closure of chiral aromatic enehydrazides. Application to the asymmetric synthesis of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines.

Eric DENIAU

^*,

Stéphane LEBRUN

¹ Unité de Catalyse et de Chimie du Solide (UCCS) UMR CNRS 8181 - Axe CCM - Equipe CASECO

Published: 30 October 2015 by MDPI in The 19th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-19-a031

Abstract:

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

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Eric DENIAU

Stéphane LEBRUN