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

Chemistry : a European Journal
Susannah C CooteThorsten Bach

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.

References

Jun 3, 2006·Natural Product Reports·Kenneth W Bentley
May 29, 2008·Angewandte Chemie·Philipp Selig, Thorsten Bach
Feb 17, 2009·Chemistry : a European Journal·Philipp SeligThorsten Bach
May 28, 2009·Angewandte Chemie·Christiane MüllerThorsten Bach
Mar 23, 2011·Organic & Biomolecular Chemistry·Aline BakowskiThorsten Bach
Apr 2, 2011·Journal of the American Chemical Society·Nicolas GuimondKeith Fagnou
Nov 15, 2011·Organic Letters·Lutz Ackermann, Sabine Fenner
Apr 20, 2012·Angewandte Chemie·Honggen Wang, Frank Glorius
Jul 26, 2012·Accounts of Chemical Research·Elizabeth H Krenske, K N Houk
May 7, 2013·Natural Product Reports·Zhong Jin
Oct 2, 2013·Journal of the American Chemical Society·Susannah C Coote, Thorsten Bach
Dec 3, 2013·Chemical Society Reviews·Cheng Yang, Yoshihisa Inoue
Apr 18, 2014·Angewandte Chemie·Nandini VallavojuJayaraman Sivaguru

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Citations

Jun 9, 2016·Journal of the American Chemical Society·Andreas TrösterThorsten Bach
Jul 25, 2019·Organic & Biomolecular Chemistry·Lisa-Marie MohrThorsten Bach
Jun 4, 2020·Chemical Communications : Chem Comm·Thomas J OsbergerDavid R Spring
Aug 7, 2017·European Journal of Organic Chemistry·Momar ToureCraig M Crews
Apr 3, 2020·The Journal of Organic Chemistry·Oleksandr P DemchukOleksandr O Grygorenko
Oct 5, 2021·Chemical Reviews·Matthew J GenzinkTehshik P Yoon

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