Novel chiral thiourea organocatalysts for the catalytic asymmetric oxaziridination

被引：22

作者：

Ji, Nan ^{[1
]}

Yuan, Jiani ^{[1
]}

Xue, Shanshan ^{[1
]}

Zhang, Junna ^{[1
]}

He, Wei ^{[1
]}

机构：

[1] Fourth Mil Med Univ, Sch Pharm, Dept Chem, Xian 710032, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Asymmetric catalysis; Oxaziridination; Cinchona alkaloids; Organic catalysis; ENANTIOSELECTIVE MICHAEL ADDITION; HIGHLY EFFICIENT; CINCHONA ALKALOIDS; CARBONYL-COMPOUNDS; MANNICH REACTIONS; AMINE-THIOUREAS; OXIDATION; CHEMISTRY; EPOXIDATION; AMINATION;

D O I：

10.1016/j.tet.2015.12.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic enantioselective oxaziridination is one of the challenging reactions in the oxidation of organic molecules. In this article, a series of novel chiral thiourea moleculars were synthesized from natural cinchona alkaloids and primary amines. By using these molecules as organocatalysts and m-chloroper-oxybenzoicacid (m-CPBA) as the oxidant, a methodology on highly enantioselective epoxidation of al-dimines has been developed. Several optically active oxaziridines have been constructed in good yields (up to 95%) and moderate to excellent enantioselectivities (up to 99% ee). A plausible transition state was also proposed. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：512 / 517

页数：6

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