Asymmetric organocatalytic allylic alkylation of Reissert compounds: a facile access to chiral 1,1-disubstituted 1,2-dihydroisoquinolines

Tian-You Qin; Wei-Wei Liao; Yan-Jing Zhang; Sean Xiao-An Zhang

doi:10.1039/C2OB27269E

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Organic & Biomolecular Chemistry

Issue 6, 2013

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Paper

Asymmetric organocatalytic allylic alkylation of Reissert compounds: a facile access to chiral 1,1-disubstituted 1,2-dihydroisoquinolines

Tian-You Qin,^a^c Wei-Wei Liao,*^a Yan-Jing Zhang^a and Sean Xiao-An Zhang*^a^b

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Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China
E-mail: wliao@jlu.edu.cn ;
Tel: (+86) 0431-85168420

State Key Lab of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China

State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, China

Org. Biomol. Chem., 2013,11, 984-990

DOI: 10.1039/C2OB27269E
Received 15 Oct 2012, Accepted 23 Nov 2012
First published online 26 Nov 2012

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The first asymmetric organocatalytic allylic alkylation of 1,2-dihydro-Reissert compounds and Morita–Baylis–Hillman (MBH) carbonates has been developed, which provided a novel protocol to construct enantioenriched functionalized 1,2-dihydroisoquinolines bearing vicinal quaternary and tertiary chiral centers at C-1 position (up to 94% ee, dr > 20:1).