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

被引：3

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

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