Chiral iminophosphoranes organocatalyzed asymmetric hydroxylation of 3-substituted oxindoles with oxaziridines

被引：15
|
作者：
Li, Baocheng [1 ,2 ]
Xu, Zhen-Jiang [1 ,2 ]
Han, Jianwei [1 ,2 ,3 ]
机构：
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Haiquan Rd, Shanghai 201418, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Ling Ling Rd, Shanghai 200032, Peoples R China
[3] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 25期
基金：
中国国家自然科学基金;
关键词：
Organocatalysis; Superbase; Iminophosphorane; Oxindoles; Hydroxylation; ENANTIOSELECTIVE ALPHA-HYDROXYLATION; BETA-KETO-ESTERS; PHASE-TRANSFER CATALYSTS; DICARBONYL COMPOUNDS; MICHAEL ADDITION; MOLECULAR-OXYGEN; DERIVATIVES; 3-HYDROXYOXINDOLE;
D O I：
10.1016/j.tetlet.2018.05.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselective hydroxylation of N-protected 3-substituted oxindoles has been developed via chiral iminophosphorane catalysis with oxaziridines as oxidants. As such, a variety of optically active 3-substituted-3-hydroxy-2-oxindoles were obtained in excellent yields (91-99%) and moderate to excellent level of enantiomeric excess (up to 94% ee). (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2412 / 2417
页数：6
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