Chiral Urea-Catalyzed Asymmetric Mannich Reaction of 3-Fluoro-oxindoles with α-Amidosulfones: Synthesis of Optically Active α-Fluoro-β-amino-oxindoles

被引：2

作者：

Zhang, Xin ^{[1
]}

Wei, Zhonglin ^{[1
]}

Cao, Jungang ^{[1
]}

Liang, Dapeng ^{[1
]}

Lin, Yingjie ^{[1
]}

Duan, Haifeng ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, Dept Organ Chem, 2699 Qianjin St, Changchun 130012, Peoples R China

来源：

SYNLETT | 2022年 / 33卷 / 05期

基金：

中国国家自然科学基金;

关键词：

Mannich reaction; 3-fluorooxindoles; alpha-fluoro-beta-amino-oxindoles; quinine-derived skeleton; urea-catalyzed catalysts; TRIFLUOROMETHYLATION; 3-FLUOROOXINDOLES; FLUORINATION;

D O I：

10.1055/a-1747-2724

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric Mannich reaction of 3-fluorooxindoles and alpha-amidosulfones catalyzed by a chiral urea catalyst derived from quinine in presence of K3PO4 was developed. Through the asymmetric reaction, a series of alpha-fluoro-beta-amino-oxindoles, containing a tertiary carbon stereocenter, could be obtained in high yields (up to 95%) with high enantioselectivity (95%) and diastereoselectivity (>99:1). Such alpha-fluoro-beta-amino-oxindole compounds are expected to become candidates in the field of medicine.

引用

页码：488 / 494

页数：7

共 3 条

[1] Catalytic Asymmetric Mono-Fluorination of α-Keto Esters: Synthesis of Optically Active β-Fluoro-α-Hydroxy and β-Fluoro-α-Amino Acid Derivatives
Suzuki, Shoko
Kitamura, Yuki
Lectard, Sylvain
Hamashima, Yoshitaka
Sodeoka, Mikiko
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (19) : 4581 - 4585
[2] Synthesis of Enantioenriched 3-Amino-3-Substituted Oxindoles by Stereoselective Mannich Reaction Catalyzed by Supported Bifunctional Thioureas.
Rodriguez-Ferrer, Patricia
Sanz-Novo, Miguel
Maestro, Alicia
Andres, Jose M.
Pedrosa, Rafael
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (15) : 3645 - 3655
[3] An Organocatalytic Mannich/Denitration Reaction for the Asymmetric Synthesis of 3-Ethylacetate-Substitued 3-Amino-2-Oxindoles: Formal Synthesis of AG-041R
Zhao, Kun
Shu, Tao
Jia, Jiaqi
Raabe, Gerhard
Enders, Dieter
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (10) : 3933 - 3936

← 1 →