Controlled β-protonation and [4+2] cycloaddition of enals and chalcones via N-heterocyclic carbene/acid catalysis: toward substrate independent reaction control

Zhenqian Fu; Hui Sun; Shaojin Chen; Bhoopendra Tiwari; Guohui Li; Yonggui Robin Chi

doi:10.1039/C2CC36564B

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Chemical Communications

Issue 3, 2013

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Controlled β-protonation and [4+2] cycloaddition of enals and chalcones via N-heterocyclic carbene/acid catalysis: toward substrate independent reaction control

Zhenqian Fu,^a Hui Sun,^b Shaojin Chen,^a Bhoopendra Tiwari,^a Guohui Li*^b and Yonggui Robin Chi*^a

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Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore
E-mail: robinchi@ntu.edu.sg ;
Fax: +65 67911961 ;
Tel: +65 65927769

State key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Rd, Dalian, P. R. China
E-mail: ghli@dicp.ac.cn ;
Fax: +86 411-84675584 ;
Tel: +86 411-84379593

Chem. Commun., 2013,49, 261-263

DOI: 10.1039/C2CC36564B
Received 10 Sep 2012, Accepted 09 Nov 2012
First published online 09 Nov 2012

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A substrate-independent selective generation of enolates over homoenolate equivalents in NHC-catalyzed reactions of enals and chalcones is disclosed. Acid co-catalysts play vital roles in control of the reaction pathways, allowing for individual access to diverse products from identical substrates.

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Zhenqian Fu
Hui Sun
Shaojin Chen
Bhoopendra Tiwari
Guohui Li
Yonggui Robin Chi

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Chemical Communications

Controlled β-protonation and [4+2] cycloaddition of enals and chalcones via N-heterocyclic carbene/acid catalysis: toward substrate independent reaction control

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Controlled β-protonation and [4+2] cycloaddition of enals and chalcones via N-heterocyclic carbene/acid catalysis: toward substrate independent reaction control

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