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Intramolecular [2+2] Photocycloaddition of Substituted Isoquinolones: Enantioselectivity and Kinetic Resolution Induced by a Chiral Template
Author(s) -
Austin Kerrie A. B.,
Herdtweck Eberhardt,
Bach Thorsten
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201103051
Subject(s) - intramolecular force , kinetic resolution , chemistry , stereochemistry , substrate (aquarium) , combinatorial chemistry , enantioselective synthesis , catalysis , organic chemistry , biology , ecology
From simple to complex : Starting from easily accessible isoquinolones 1 (X=Br, OH), complex cyclobutane photoproducts such as compound 2 can be obtained with high enantioselectivity (88–96 % ee ) through the use of a chiral template. Compound 3 , which was isolated in 53 % ee starting from a racemic substrate, is the product of a unique, unprecedented kinetic resolution process.