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

被引：7

作者：

Nagato, Yuya ^{[1
,2
]}

Kiyokawa, Mari ^{[1
,2
]}

Ueki, Yusuke ^{[1
,2
]}

Kikuchi, Jun ^{[3
]}

Ohmatsu, Kohsuke ^{[1
,2
]}

Terada, Masahiro ^{[3
]}

Ooi, Takashi ^{[1
,2
]}

机构：

[1] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Nagoya, Aichi 4648601, Japan

[2] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648601, Japan

[3] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 9卷 / 04期

关键词：

hybrid catalysis; d-amino acid; dynamic kinetic resolution; palladium; allylic alkylation; DYNAMIC KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; PHENYLALANINE DERIVATIVES; C-O; STEREOINVERSION; PYRAZOL-5-ONES; ALKYLATION; ALLYLATION; OXIDATION; ALCOHOLS;

D O I：

10.1002/ajoc.202000067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 Bronsted 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.

引用

页码：561 / 565

页数：5