Issue 6, 2013
From the journal:

Organic & Biomolecular Chemistry

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

Tian-You Qin,ac   Wei-Wei Liao,*a   Yan-Jing Zhanga  and  Sean Xiao-An Zhang*ab  

* Corresponding authors

a 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

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

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

Abstract

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).

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

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Article information

DOI
https://doi.org/10.1039/C2OB27269E
Article type
Paper
Submitted
15 Oct 2012
Accepted
23 Nov 2012
First published
26 Nov 2012

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

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

T. Qin, W. Liao, Y. Zhang and S. X. Zhang, Org. Biomol. Chem., 2013, 11, 984 DOI: 10.1039/C2OB27269E

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