Stereospecific Formal [3+2] Dipolar Cycloaddition of Cyclopropanes with Nitrosoarenes: An Approach to Isoxazolidines

被引：149

作者：

Chakrabarty, Shyamal ^{[1
]}

Chatterjee, Indranil ^{[1
]}

Wibbeling, Birgit ^{[1
]}

Daniliuc, Constantin Gabriel ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, NRW Grad Sch Chem, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 23期

关键词：

cycloadditions; cyclopropanes; heterocycles; nitrosoarene; stereoselective synthesis; DONOR-ACCEPTOR CYCLOPROPANES; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; DIVERSITY-ORIENTED SYNTHESIS; DIELS-ALDER REACTIONS; ENOL SILYL ETHERS; ENANTIOSELECTIVE SYNTHESIS; RING EXPANSION; SUBSTITUTED CYCLOPROPANES; STEREOSELECTIVE-SYNTHESIS; ACTIVATED CYCLOPROPANES;

D O I：

10.1002/anie.201400885

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The MgBr2-catalyzed formal [3+2] cycloaddition of donor-acceptor activated cyclopropanes with nitrosoarenes offers a novel approach to various structurally diverse isoxazolidines. The reactions, which are experimentally easy to conduct, occur with complete stereospecificity and perfect control of regioselectivity. Product isoxazolidines can be readily transformed into a-amino lactones by reductive or decarboxylative N-O cleavage and subsequent lactonisation, and the N-aryl bond cleavage is also possible under oxidative conditions.

引用

页码：5964 / 5968

页数：5

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