Non-Enzymatic Hybrid Catalysis for Stereoconversion of l-Amino Acid Derivatives to d-Isomers

Yuya Nagato, Mari Kiyokawa, Yusuke Ueki, Jun Kikuchi, Kohsuke Ohmatsu, Masahiro Terada, Takashi Ooi

研究成果: Article査読

2 被引用数 (Scopus)

抄録

A catalytic transformation of N-unprotected l-amino esters to N-protected d-amino esters was developed. The combined use of a heteroaromatic aldehyde, Lewis acid, palladium complex, and chiral Brønsted acid was a key factor for the successful operation of this catalytic system. The synergistic cooperation of an appropriate aldehyde and Lewis acid was crucial for promoting an efficient racemization of l-amino esters, while the combination of a palladium complex and chiral phosphoric acid enabled dynamic kinetic resolution through asymmetric N-allylation, providing N-protected d-amino esters in good yields with up to 97 : 3 er. Following appropriate deprotection processes, d-amino acids were obtained without loss of enantiomeric purity.

本文言語English
ページ(範囲)561-565
ページ数5
ジャーナルAsian Journal of Organic Chemistry
9
4
DOI
出版ステータスPublished - 2020 4 1

ASJC Scopus subject areas

  • Organic Chemistry

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