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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 11: 3693 - 3703

DOI: https://doi.org/10.6023/cjoc202204047

ARTICLES

Asymmetric Transfer Hydrogenation of α-Aryl Amidates Using Methanol as Hydrogen Source

  • Ting Wang ,
  • Jingchao Chen ,
  • Lun Wang ,
  • Zheting Wang ,
  • Baomin Fan
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  • aKey Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650500
    bSchool of Chemistry and Environment, Yunnan Minzu University, Kunming 650500
*E-mail: ;

Received date: 2022-04-18

  Revised date: 2022-07-11

  Online published: 2022-08-10

Supported by

National Natural Science Foundation of China(21961045); National Natural Science Foundation of China(22061048)

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Abstract

As a kind of amino acid derivatives, chiral arylglycine not only has very important application value in the field of organic synthesis, but also serves as the key structure of many chiral drugs and biologically active compounds. A practical and economical method for the preparation of chiral α-arylglycines is reported herein. By using methanol as the hydrogen source, a series of chiral α-arylglycine derivatives were prepared by asymmetric transfer hydrogenation of α-aryl imine esters with Pd/Zn co-catalyzed system. By switching the hydrogen source to deuterated methanol, a series of chiral deuterated a-arylglycine derivatives were obtained. The catalytic system featured with good substrate suitability, and the product was obtained in up to 93% yield with up to 92% enantioselectivity, and the deuteration incorporation rate is up to 94%. The present method has provided an efficient and economic method for the synthesis of valuable deuterium-labeled chiral amino acids.

Key words： methanol; imino acid; deuterium amino acid; asymmetric transfer hydrogenation

Cite this article

Ting Wang , Jingchao Chen , Lun Wang , Zheting Wang , Baomin Fan . Asymmetric Transfer Hydrogenation of α-Aryl Amidates Using Methanol as Hydrogen Source[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3693 -3703 . DOI: 10.6023/cjoc202204047

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