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Issue 53, 2020
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Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes

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Abstract

Constructing eight-membered rings, especially in an enantioselective manner, is a challenging task due to unfavorable enthalpic and entropic barriers of the transition states during the formation process. Here we report an asymmetric [4+4] annulation reaction of diverse 1-azadienes and β-substituted cyclobutenones under the catalysis of modified cinchona alkaloids, by the in situ generation of ring-opened ammonium dienolate intermediates. A spectrum of heteroarene- or indene-fused eight-membered lactams are obtained in fair to excellent yields with remarkable enantioselectivities (up to 99% yield, 99% ee).

Graphical abstract: Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes

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Supplementary files

Article information


Submitted
20 Apr 2020
Accepted
21 May 2020
First published
21 May 2020

Chem. Commun., 2020,56, 7257-7260
Article type
Communication

Modified cinchona alkaloid-catalysed enantioselective [4+4] annulations of cyclobutenones and 1-azadienes

B. Jiang, W. Du and Y. Chen, Chem. Commun., 2020, 56, 7257
DOI: 10.1039/D0CC02836C

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