Asymmetric Access of γ-Amino Acids and γ-Amino Phosphonic Acid Derivatives via Copper-Catalyzed Enantioselective and Regioselective Hydroamination

Zhiping Yang, Qingwei Du, Yanxin Jiang, Jun Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

γ-Aminobutyric acid is a major inhibitory neurotransmitter in the mammalian central nervous system that plays a substantial role in brain disorders. γ-Amino phosphonic acid is a unique surrogate of both natural and unnatural γ-amino acid. Because of their unique biological activity, γ-amino acid and γ-amino phosphonic acid derivatives have attracted considerable attention. However, an efficient and straightforward method for constructing chiral γ-substituted-γ-amino acid and γ-amino phosphonic acid derivatives remains a long-standing challenge. Herein, a highly efficient, versatile, and universal Cu-catalyzed asymmetric hydroamination of cinnamyl esters, cinnamyl phosphonates, and cinnamyl phosphine oxides is presented for accessing γ-amino acid and γ-amino phosphonic acid derivatives in good yields with high levels of enantiocontrol and regioselectivity.

Original languageEnglish
Pages (from-to)1901-1911
Number of pages11
JournalCCS Chemistry
Volume4
Issue number6
Early online date24 Aug 2021
DOIs
Publication statusPublished - Jun 2022

Scopus Subject Areas

  • Chemistry(all)

User-Defined Keywords

  • amino phosphine
  • asymmetric catalysis
  • copper
  • hydroamination
  • γ-amino acid

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