Iron(II)-Catalyzed Intramolecular Aminohydroxylation of Olefins with Functionalized Hydroxylamines

被引：143

作者：

Liu, Guan-Sai ^{[1
]}

Zhang, Yong-Qiang ^{[1
]}

Yuan, Yong-An ^{[1
]}

Xu, Hao ^{[1
]}

机构：

[1] Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 09期

关键词：

CATALYZED ASYMMETRIC EPOXIDATION; C-H AMINATION; TETHERED AMINOHYDROXYLATION; ENANTIOSELECTIVE AZIRIDINATION; UNFUNCTIONALIZED OLEFINS; ALKENE AZIRIDINATION; MECHANISTIC INSIGHT; COUPLING REACTIONS; ORGANIC-SYNTHESIS; IRON;

D O I：

10.1021/ja311923z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A diastereoselective aminohydroxylation of olefins with a functionalized hydroxylamine is catalyzed by new iron(II) complexes. This efficient intramolecular process readily affords synthetically useful amino alcohols with excellent selectivity (dr up to > 20:1). Asymmetric catalysis with chiral iron(II) complexes and preliminary mechanistic studies reveal an iron nitrenoid is a possible intermediate that can undergo either aminohydroxylation or aziridination, and the selectivity can be controlled by careful selection of counteranion/ligand combinations.

引用

页码：3343 / 3346

页数：4

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