Catalytic Asymmetric Ring-Opening Reactions of Aziridines with 3-Aryl-Oxindoles

被引：36

作者：

Wang, Linqing ^{[1
]}

Li, Dan ^{[1
]}

Yang, Dongxu ^{[1
]}

Wang, Kezhou ^{[1
]}

Wang, Jie ^{[1
]}

Wang, Pengxin ^{[1
]}

Su, Wu ^{[2
]}

Wang, Rui ^{[1
,3
]}

机构：

[1] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Shenzhen Inst Adv Technol, Inst Biomed & Biotechnol, Guangdong Key Lab Nanomed, Shenzhen 518055, Guangdong, Peoples R China

[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2016年 / 11卷 / 05期

关键词：

aziridines; 3,3 '-fluorinated-binol; magnesium catalysis; oxindoles; ring-opening reactions; MANNICH-TYPE REACTION; DIELS-ALDER REACTION; MESO-AZIRIDINES; CONJUGATE ADDITION; ENANTIOSELECTIVE DESYMMETRIZATION; EFFICIENT CONSTRUCTION; N-SULFONYLAZIRIDINES; ALLYLIC ALKYLATION; PHOSPHONIUM SALTS; MICHAEL ADDITION;

D O I：

10.1002/asia.201501369

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective ring-opening alkylation reaction between 3-aryl-oxindole and N-(2-picolinoyl) aziridine has been realized for the first time. The reaction is efficiently mediated by a simple in-situ-generated magnesium catalyst and 3,3-fluorinated-BINOL (BINOL=1,1-binaphthalene-2,2-diol) has been identified as a powerful chiral ligand. Notably, the fluorine atom on the chiral ligand plays a key role in providing the desired chiral 3-alkyl-3-aryl oxindoles with excellent enantioselectivities.

引用

页码：691 / 695

页数：5

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