Copper-Catalyzed Asymmetric Hydroamination: A Unified Strategy for the Synthesis of Chiral β-Amino Acid and Its Derivatives

被引：31

作者：

Zhang, Ge ^{[1
]}

Liang, Yujie ^{[2
]}

Qin, Tao ^{[1
]}

Xiong, Tao ^{[1
]}

Liu, Shuyu ^{[1
]}

Guan, Wei ^{[2
]}

Zhang, Qian ^{[1
,3
]}

机构：

[1] Northeast Normal Univ, Dept Chem, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China

[2] Northeast Normal Univ, Inst Funct Mat Chem, Dept Chem, Changchun 130024, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CCS CHEMISTRY | 2021年 / 3卷 / 07期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; reversal hydroamination; chiral beta-amino acid and its derivatives; copper catalysis; Michael acceptors; ENANTIOSELECTIVE CONJUGATE ADDITION; O-BENZYLHYDROXYLAMINE; ALKENES; HYDRIDE; ROUTE; HETEROCYCLES; REDUCTION; COMPLEXES; ALKYNES; ESTERS;

D O I：

10.31635/ccschem.020.202000434

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric aza-Michael represents one of the most convenient and atom-economical approaches for the rapid construction of biologically active chiral beta-amino acid frameworks. However, the direct enantioselective addition of nitrogen-based nucleophiles to intrinsically low reactivity of alpha, beta-unsaturated carboxylic acid, ester, and amide, as well as simple alpha,beta-unsaturated nitrile, remains a long-standing challenge. Herein, we report a unified Cu-catalyzed asymmetric reversal hydroamination, capable of direct preparation of a series of beta-amino acid, ester, amide, and nitrile in a highly regio- and enantioselective manner, without the requirement of traditional preinstallation of stoichiometric quantities of auxiliaries.

引用

页码：1737 / 1745

页数：9

共 73 条

[21] A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination [J].