Enantioselective template-directed [2+2] photocycloadditions of isoquinolones:scope, mechanism and synthetic applications

Coote, Susannah and Pöthig, Alexander and Bach, Thorsten (2015) Enantioselective template-directed [2+2] photocycloadditions of isoquinolones:scope, mechanism and synthetic applications. Chemistry - A European Journal, 21 (18). 6906–6912. ISSN 0947-6539

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Abstract

A strategy for the enantioselective [2+2] photocycloaddition of isoquinolones with alkenes is presented, in which the formation of a supramolecular complex between a chiral template and the substrate ensures high enantioface differentiation by shielding one face of the substrate. Fifteen different electron-deficient alkenes and ten different substituted isoquinolones undergo efficient photocycloaddition, yielding the cyclobutane products in excellent yields and with outstanding regio-, diastereo- and enantioselectivities (up to 99 % ee). The mechanism of the reaction is investigated by means of triplet sensitization/quenching and radical clock experiments, the results of which are consistent with the involvement of a triplet excited state and a 1,4-biradical intermediate. The variety of functionalized cyclobutanes obtained using this approach can be further increased by straightforward synthetic transformations of the photoadducts, allowing rapid access to libraries of compounds for various applications.

Item Type: Journal Article
Journal or Publication Title: Chemistry - A European Journal
Uncontrolled Keywords: /dk/atira/pure/subjectarea/asjc/1600
Subjects:
ID Code: 73867
Deposited By: ep_importer_pure
Deposited On: 31 Jul 2015 10:46
Refereed?: Yes
Published?: Published
Last Modified: 17 Feb 2020 07:03
URI: https://eprints.lancs.ac.uk/id/eprint/73867

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