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

2 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

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Amino acids
Hydrolysis
Esters
Amino Acids
Stereoselectivity
Catalysts
Kinetics
Quinine
Ammonium Compounds
Discrete Fourier transforms
Salts
Molecules

All Science Journal Classification (ASJC) codes

  • Catalysis

Cite this

Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis. / Yamamoto, Eiji; Wakafuji, Kodai; Furutachi, Yuho; Kobayashi, Kaoru; Kamachi, Takashi; Tokunaga, Makoto.

In: ACS Catalysis, Vol. 8, No. 7, 06.07.2018, p. 5708-5713.

Research output: Contribution to journalArticle

Yamamoto, Eiji ; Wakafuji, Kodai ; Furutachi, Yuho ; Kobayashi, Kaoru ; Kamachi, Takashi ; Tokunaga, Makoto. / Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis. In: ACS Catalysis. 2018 ; Vol. 8, No. 7. pp. 5708-5713.
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