Stereoselective Lewis Base-Catalyzed Asymmetric Hydrosilylation of α-Acetamido-β-enamino Esters: Straightforward Approach for the Construction of α,β-Diamino Acid Derivatives

被引：24

作者：

Jiang, Yan ^{[1
,2
]}

Chen, Xing ^{[1
,2
]}

Hu, Xiao-Yan ^{[1
,2
]}

Shu, Chang ^{[1
,2
]}

Zhang, Yong-Hong ^{[1
,2
]}

Zheng, Yong-Sheng ^{[1
,2
]}

Lian, Chun-Xia ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

机构：

[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chiraltechnol Sichuan Pr, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 10期

关键词：

amino acids; asymmetric catalysis; hydrosilylation; Lewis bases; MANNICH-TYPE REACTION; GLYCINE SCHIFF-BASES; ENANTIOSELECTIVE SYNTHESIS; AMINO-ACIDS; STEREOCONTROLLED SYNTHESIS; ANTITUMOR ANTIBIOTICS; SELECTIVE SYNTHESES; EFFICIENT SYNTHESIS; AROMATIC KETIMINES; IMINES;

D O I：

10.1002/adsc.201300184

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The Lewis base-organocatalyzed asymmetric hydrosilylation of alpha-acetamido-beta-enamino esters was investigated. Among various chiral Lewis base catalysts, a novel catalyst derived from L-serine was found to be the most efficient one which can promote the reaction to afford a series of alpha,beta-diamino acid derivatives with high yields (up to 99%), excellent enantioselectivities (up to 98% ee) and moderate diastereoselectivities (up to 80: 20 dr). The absolute configuration of one of the products was determined by the X-ray crystallographic analysis. In addition, the mechanism and the transition state of the reaction were proposed.

引用

页码：1931 / 1936

页数：6

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