Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

被引：8

作者：

Inada, Haruki ^{[1
]}

Shibuya, Masatoshi ^{[1
]}

Yamamoto, Yoshihiko ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Pharmaceut Sci, Dept Basic Med Sci, Chikusa Ku, Furo Cho, Nagoya, Aichi 4648601, Japan

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 03期

关键词：

ASYMMETRIC BIOMIMETIC TRANSAMINATION; X=Y-ZH SYSTEMS; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITION REACTIONS; POTENTIAL 1,3-DIPOLES; HIGHLY EFFICIENT; KETONIC ACIDS; HYDROXY ACIDS; CATALYSIS; OXIDATION;

D O I：

10.1021/acs.orglett.8b03910

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical telescoping three-step process for the syntheses of alpha-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free alpha-amino acids without any protection/deprotection step. This method was also effective for the preparation of a N-15-labeled alpha-amino acid. 1,2-Diols bearing alpha,beta-unsaturated ester moieties afforded bicyclic alpha-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant alpha-amino acids are resolvable by aminoacylases with almost complete selectivity.

引用

页码：709 / 713

页数：5

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