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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 9: 3188 - 3195

DOI: https://doi.org/10.6023/cjoc202303035

Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide

  • Chun-Xia Cheng ,
  • Lu-Ping Wu ,
  • Feng Sha ,
  • Xin-Yan Wu
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  • Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237
* E-mail:

Received date: 2023-03-23

  Revised date: 2023-05-18

  Online published: 2023-06-07

Supported by

Natural Science Foundation of Shanghai(19ZR1412300); Shanghai Pujiang Program(18PJD010)

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Abstract

An organocatalytic enantioselective direct vinylogous allylic alkylation between coumarins and racemic Morita- Baylis-Hillman carbonates has been developed. With 10~15 mol% a chiral cyclohexane-based phosphine-amide C10, a wide range of densely functionalized coumarin derivatives have been achieved in 87%~99% yields and up to 98% ee.

Key words： allylic alkylation; asymmetric catalysis; chiral phosphine; organocatalysis; vinylogous reaction

Cite this article

Chun-Xia Cheng , Lu-Ping Wu , Feng Sha , Xin-Yan Wu . Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide[J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3188 -3195 . DOI: 10.6023/cjoc202303035

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