Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis

Eiji Yamamoto, Kodai Wakafuji, Yuho Furutachi, Kaoru Kobayashi, Takashi Kamachi, Makoto Tokunaga

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl3/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%) with up to 96:4 er. Experimental and computational mechanistic studies using DFT calculation and pseudotransition state (pseudo-TS) conformational search afforded a TS model accounting for the origin of the stereoselectivity. The model suggested π-stacking and H-bonding interactions play essential roles in stabilizing the TS structures.

Original languageEnglish
Pages (from-to)5708-5713
Number of pages6
JournalACS Catalysis
Volume8
Issue number7
DOIs
Publication statusPublished - Jul 6 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis'. Together they form a unique fingerprint.

Cite this