Organocatalytic asymmetric Michael addition of pyrazoleamides to β-phthalimidonitroethene

被引：9

作者：

Luo, Yuan ^{[1
,3
]}

Xie, Ke-Xin ^{[2
]}

Yue, Deng-Feng ^{[1
,3
]}

Zhang, Xiao-Mei ^{[1
]}

Xu, Xiao-Ying ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Sichuan, Peoples R China

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

来源：

TETRAHEDRON | 2017年 / 73卷 / 43期

基金：

中国国家自然科学基金;

关键词：

Michael addition; Pyrazoleamides; beta-Phthalimidonitroethene; beta-Amino acid derivatives; CYCLIZATION CASCADE REACTION; AMINO ACID-DERIVATIVES; PROTECTED; 2-AMINO-1-NITROETHENES; BETA; GAMMA-UNSATURATED AMIDES; ENANTIOSELECTIVE SYNTHESIS; TRIFLUOROETHYL THIOESTERS; CONSTRUCTION; OXINDOLES; PEPTIDES; ESTERS;

D O I：

10.1016/j.tet.2017.09.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly organocatalyzed asymmetric Michael addition reaction of pyrazoleamides to beta-phthalimidonitroethene has been developed with a chiral bifunctional thiourea-tertiary amine as the catalyst. A wide range of gamma-nitro beta-amino amides were readily obtained in good to excellent yields with high diastereo-and enantioselectivities (up to 99% yield, 99% ee and >20:1 dr). The large scale experiment and transformation of the product have also been demonstrated. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：6217 / 6222

页数：6

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