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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2904 - 2911

DOI: https://doi.org/10.6023/cjoc202005037

Catalytic Asymmetric Synthesis of β,γ-Alkynyl α-Amino Esters via Chemo- and Enantio-selective Transfer Hydrogenation

  • Zhang Lu ,
  • Liu Aiqin ,
  • Liu Huazheng ,
  • Wan Renzhong ,
  • Sun Shutao ,
  • Liu Lei
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  • a College of Animal Science and Veterinary Medicine, Shandong Agricultural University, Taian, Shandong 271018;
    b School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100;
    c Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250062

Received date: 2020-05-15

  Revised date: 2020-06-03

  Online published: 2020-06-13

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21722204, 21971148).

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Abstract

An effective chemo- and enantioselective transfer hydrogenation of β,γ-alkynyl α-imino esters to prepare optically pure β,γ-alkynyl α-amino esters has been described. The excellent chemoselectivity was achieved by using chiral phosphoric acid catalyzed asymmetric reduction with benzothiazoline as hydride donor. The reaction exhibited good functional group tolerance, providing a range of optically active non-natural amino esters with excellent enantioselectivity.

Key words： β,γ-alkynyl α-amino ester; chemoselectivity; enantioselectivity; transfer hydrogenation; benzothiazoline

Cite this article

Zhang Lu , Liu Aiqin , Liu Huazheng , Wan Renzhong , Sun Shutao , Liu Lei . Catalytic Asymmetric Synthesis of β,γ-Alkynyl α-Amino Esters via Chemo- and Enantio-selective Transfer Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2020 , 40(9) : 2904 -2911 . DOI: 10.6023/cjoc202005037

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