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
收藏
页码：6217 / 6222
页数：6
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