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Issue 56, 2016
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Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

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Abstract

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Graphical abstract: Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

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Article information


Submitted
14 Feb 2016
Accepted
16 Jun 2016
First published
16 Jun 2016

Chem. Commun., 2016,52, 8757-8760
Article type
Communication

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

M. Zhang, S. Yu, F. Hu, Y. Liao, L. Liao, X. Xu, W. Yuan and X. Zhang, Chem. Commun., 2016, 52, 8757
DOI: 10.1039/C6CC01200K

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