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Synthesis
DOI: 10.1055/a-2779-0844
Paper

Synthesis of β3 -Amino Acid Derivatives via the Regioselective Carbozincation of Ynamides and Subsequent Asymmetric Hydrogenation

Authors

  • Sayaka Ohrui

    1   Faculty of Pharmaceutical Sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Sugako Matsui

    1   Faculty of Pharmaceutical Sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Keisuke Yoshida

    1   Faculty of Pharmaceutical Sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Noriko Oshida

    1   Faculty of Pharmaceutical Sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Masanori Tayu

    1   Faculty of Pharmaceutical Sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Nozomi Saito 

    1   Faculty of Pharmaceutical Sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

Supported by: Japan Society for the Promotion of Science 21K06484
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β-Amino acids are key constituents of various bioactive molecules, pharmaceuticals, and natural products, thereby highlighting their importance in organic chemistry. A novel synthetic method was developed for β3 -amino acid derivatives based on the use of ynamides bearing ester moieties. Initially, the Cu-catalyzed regioselective carbozincation of these ynamides afforded β-aminoacrylic acid esters bearing a substituent at the β-position. Subsequent asymmetric hydrogenation using a rhodium catalyst and the Walphos ligand yielded the corresponding β3-amino acid derivatives.



Publication History

Received: 08 November 2025

Accepted after revision: 24 December 2025

Accepted Manuscript online:
24 December 2025

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