EventsThe 19th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-19-a031
This submission belongs to the session a. General Organic Synthesis of the event The 19th International Electronic Conference on Synthetic Organic Chemistry
Published date
30 Oct, 2015
Citation
Eric DENIAU, Stéphane LEBRUN, Asymmetric photoinduced electrocyclic ring closure of chiral aromatic enehydrazides. Application to the asymmetric synthesis of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines., in Proceedings of The 19th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2015, MDPI: Basel, Switzerland, 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 1
Stéphane LEBRUN 1
1. Unité de Catalyse et de Chimie du Solide (UCCS) UMR CNRS 8181 - Axe CCM - Equipe CASECO
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
Manuscript
ecsoc_19_photochemistry.pdf
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