Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[b,f][1,4]oxazepines: Highly Enantioselective Construction of Tetrasubstituted C-F Stereocenters

被引：22

作者：

Li, Bing-Yu ^{[1
]}

Lin, Ye ^{[1
]}

Du, Da-Ming ^{[1
]}

机构：

[1] Beijing Inst Technol, Sch Chem & Chem Engn, Beijing 100081, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期

基金：

中国国家自然科学基金;

关键词：

HIV-1; REVERSE-TRANSCRIPTASE; NONNUCLEOSIDE INHIBITORS; MICHAEL ADDITION; FLUORINE; DERIVATIVES; ACCESS; STEREOSELECTIVITY; DIBENZOXAZEPINES; PHARMACOLOGY; NITROALKENES;

D O I：

10.1021/acs.joc.9b01507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Fluorooxindoles and the dibenzo[b,f][1,4]oxazepane scaffolds are important pharmacophores that have important application in medicinal chemistry. An organocatalyzed asymmetric Mannich reaction of 3-fluorooxindoles with dibenzo[b,f][1,4]oxazepines affording various seven-member cyclic amines containing chiral tetrasubstituted C-F stereocenters was developed. These reactions which were catalyzed by a bifunctional Cinchona alkaloid-derived thiourea catalyst afforded a wide range of substrates in moderate to high yields with excellent diastereo- and enantioselectivities (up to 88% yield, >20:1 dr and >99% ee). A feasible reaction mechanism was also proposed.

引用

页码：11752 / 11762

页数：11

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