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

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)561-565
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume9
Issue number4
DOIs
Publication statusPublished - 2020 Apr 1

Keywords

  • allylic alkylation
  • d-amino acid
  • dynamic kinetic resolution
  • hybrid catalysis
  • palladium

ASJC Scopus subject areas

  • Organic Chemistry

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