脯氨酸作为路易斯碱催化剂：通过[3 + 2]环加成反应非对映选择性合成异恶唑啉-N-氧化物。

Proline as Lewis base catalyst: diastereoselective synthesis of isoxazoline-N-oxide through [3 + 2] cycloaddition.

作者信息

Duan Haifeng, Sun Xiaohua, Liao Wenyan, Petersen Jeffrey L, Shi Xiaodong

机构信息

C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.

出版信息

Org Lett. 2008 Sep 18;10(18):4113-6. doi: 10.1021/ol801656y. Epub 2008 Aug 23.

DOI:10.1021/ol801656y

PMID:18722449

Abstract

A catalytic cascade synthesis of isoxazoline-N-oxide was developed through proline-catalyzed nitroalkene activation. A large substrate scope was obtained with good to excellent yields. Mechanistic studies revealed intramolecular cyclization as the rate-determining step, giving only trans isomers in all cases.

摘要

通过脯氨酸催化的硝基烯烃活化反应，开发了一种异恶唑啉-N-氧化物的催化级联合成方法。该方法底物范围广，产率良好至优异。机理研究表明分子内环化是速率决定步骤，在所有情况下均只生成反式异构体。