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

共 83 条

[41] Amidoglycosylation via metal-catalyzed internal nitrogen atom delivery [J].

Levites-Agababa, E ;

Menhaji, E ;

Perlson, LN ;

Rojas, CM .

ORGANIC LETTERS, 2002, 4 (05) :863-865

[42] Catalytic asymmetric aminohydroxylation (AA) of olefins [J].

Li, GG ;

Chang, HT ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :451-454

[43] ASYMMETRIC ALKENE AZIRIDINATION WITH READILY AVAILABLE CHIRAL DIIMINE-BASED CATALYSTS [J].

LI, Z ;

CONSER, KR ;

JACOBSEN, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5326-5327

[44] Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and SN2 C-O bond formation [J].

Liu, Guosheng ;

Stahl, Shannon S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7179-7181

[45] Metal-Free Highly Regioselective Aminotrifluoroacetoxylation of Alkenes [J].

Lovick, Helena M. ;

Michael, Forrest E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1249-+

[46] Copper-Catalyzed Olefin Aminoacetoxylation [J].

Mancheno, Danny E. ;

Thornton, Aaron R. ;

Stoll, Armin H. ;

Kong, Aidi ;

Blakey, Simon B. .

ORGANIC LETTERS, 2010, 12 (18) :4110-4113

[47] Activation of N-sulfonyl oxaziridines using copper(II) catalysts:: Aminohydroxylations of styrenes and 1,3-dienes [J].

Michaelis, David J. ;

Ischay, Michael A. ;

Yoon, Tehshik P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (20) :6610-6615

[48] Copper(II)-catalyzed aminohydroxylation of olefins [J].

Michaelis, David J. ;

Shaffer, Christopher J. ;

Yoon, Tehshik P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1866-+

[49] Oxaziridine-mediated enantioselective aminohydroxylation of styrenes catalyzed by copper(II) bis(oxazoline) complexes [J].

Michaelis, David J. ;

Williamson, Kevin S. ;

Yoon, Tehshik P. .

TETRAHEDRON, 2009, 65 (26) :5118-5124

[50] Enantioselective Synthesis of Sphingadienines and Aromatic Ceramide Analogs [J].

Moreno, Maria ;

Murruzzu, Caterina ;

Riera, Antoni .

ORGANIC LETTERS, 2011, 13 (19) :5184-5187

← 1 2 3 4 5 6 7 8 9 →