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Modified Cinchona Alkaloid‐Catalysed Enantioselective [4 + 4] Annulations of Cyclobutenones and 1-Azadienes

Abstract

Constructing eight-membered rings, especially in an enantioselective manner, is a challenge 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 in situ generating ring-opened ammonium dienolate intermediates. A spectrum of heteroarene- or indene-fused eight-membered lactams are furnished in fair to excellent yields with remarkable enantioselectivity (up to 99% yield, 99% ee).

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Article information


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

Chem. Commun., 2020, Accepted Manuscript
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, Accepted Manuscript , DOI: 10.1039/D0CC02836C

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