Nickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Nitrones with α,β-Unsaturated Acylcarboxylates

被引：17

作者：

Xie, Lei ^{[1
]}

Yu, Xuan ^{[1
]}

Li, Jiaqi ^{[1
]}

Zhang, Zhenhua ^{[1
]}

Qin, Zhaohai ^{[1
]}

Fu, Bin ^{[1
]}

机构：

[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 03期

关键词：

Asymmetric synthesis; Cycloaddition; Heterocycles; Nickel; Nitrones; CARBON QUATERNARY STEREOCENTERS; FRIEDEL-CRAFTS ALKYLATION; BINAPHTHYLDIIMINE-NI(II) COMPLEXES; TRIFLATE COMPLEX; ACID; DERIVATIVES; INDOLES; 3-ALKENOYL-2-OXAZOLIDINONES; CONSTRUCTION; CHEMISTRY;

D O I：

10.1002/ejoc.201601540

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly enantioselective 1,3-dipolar cycloaddition of nitrones with alpha,beta-unsaturated acylcarboxylates was realized for the first time by using a chiral bis(indano-oxazoline)-based Ni complex. The reaction proceeded smoothly under mild conditions and provided isoxazolidines with three contiguous stereocenters in high yields with excellent diastereoselectivities (> 20: 1 dr) and enantioselectivities (up to 99 % ee). The reaction was scaled up to the gram scale, and the products were readily transformed into gamma-amino alcohols and other potentially bioactive compounds.

引用

页码：657 / 661

页数：5

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