Aminomethylation of Enals through Carbene and Acid Cooperative Catalysis: Concise Access to β2-Amino Acids

被引：99

作者：

Xu, Jianfeng ^{[1
]}

Chen, Xingkuan ^{[1
]}

Wang, Ming ^{[1
]}

Zheng, Pengcheng ^{[1
,2
]}

Song, Bao-An ^{[2
]}

Chi, Yonggui Robin ^{[1
,2
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

[2] Guizhou Univ, Key Lab Green Pesticide & Agr Bioengn, Lab Breeding Base Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 17期

基金：

中国国家自然科学基金; 新加坡国家研究基金会;

关键词：

amino acids; asymmetric synthesis; Bronsted acid; N-heterocyclic carbenes; organocatalysis; N-HETEROCYCLIC CARBENE; PEPTIDE-BASED CATALYSTS; AZA-BENZOIN REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; STEREOSELECTIVE-SYNTHESIS; ORGANOCATALYTIC ACTIVATION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ANNULATION REACTIONS; ENOLATE EQUIVALENTS;

D O I：

10.1002/anie.201412132

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent, organocatalytic asymmetric aminomethylation of alpha,beta -unsaturated aldehydes by N-heterocyclic carbene (NHC) and (in situ generated) Bronsted acid cooperative catalysis is disclosed. The catalytically generated conjugated acid from the base plays dual roles in promoting the formation of azolium enolate intermediate, formaldehydederived iminium ion (as an electrophilic reactant), and methanol (as a nucleophilic reactant). This redox-neutral strategy is suitable for the scalable synthesis of enantiomerically enriched beta(2)-amino acids bearing various substituents.

引用

页码：5161 / 5165

页数：5

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