Efficient Synthesis of β-Hydroxy-α-Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes

被引：35

作者：

Chen, Xiaohong ^{[1
]}

Zhu, Yin ^{[1
]}

Qiao, Zhen ^{[1
]}

Xie, Mingsheng ^{[1
]}

Lin, Lili ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 33期

基金：

中国国家自然科学基金;

关键词：

aldol reaction; amino acids; asymmetric catalysis; nickel; nitrogen oxides; ENANTIOSELECTIVE MICHAEL ADDITIONS; INTRAMOLECULAR 4+2 CYCLOADDITIONS; DIELS-ALDER REACTION; CONJUGATE ADDITION; LEWIS-ACID; 1,3-DICARBONYL COMPOUNDS; CONVENIENT SYNTHESIS; NICKEL; COMPLEXES; ESTERS;

D O I：

10.1002/chem.201000284

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98%) with excellent diastereo- (up to > 99: 1 d.r.) and enantio- selectivities (up to > 99% ee). A variety of aromatic, heteroaromatic, alpha,beta-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol% L-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air- tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.

引用

页码：10124 / 10129

页数：6

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