A chiral rhodium carboxamidate catalyst for enantioselective C-H amination

被引：224

作者：

Zalatan, David N. ^{[1
]}

Du Bois, J. ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 29期

关键词：

D O I：

10.1021/ja8031955

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rh-2(S-nap)(4), a chiral dirthodium tetracarboxamidate complex, has been developed and shown to be an effective catalyst for the asymmetric, intramolecular C-H amination of sulfamate esters. Enantiomeric excesses range from 60-99% for a collection of disparately substituted 3-arylpropylsulfamates. In addition, Rh-2(S-nap)(4) is found to promote chemoselective allylic C-H oxidation of unsaturated sulfamates, a property not observed with other dirhodium complexes tested to date.

引用

页码：9220 / +

页数：3

共 26 条

[1] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].

Davies, Huw M. L. ;

Manning, James R. .

NATURE, 2008, 451 (7177) :417-424

[2]

Doyle M. P., 1997, MODERN CATALYTIC MET

[3] Perspective on dirhodium carboxamidates as catalysts [J].

Doyle, Michael P. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9253-9260

[4] The influence of ligands on dirhodium(II) on reactivity and selectivity in metal carbene reactions [J].

Doyle, MP ;

Ren, T .

PROGRESS IN INORGANIC CHEMISTRY, VOL 49, 2001, 49 :113-168

[5] Synthesis of 1,3-difunctionalized amine derivatives through selective C-H bond oxidation [J].

Espino, CG ;

Wehn, PM ;

Chow, J ;

Du Bois, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6935-6936

[6]

Espino CG, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P379, DOI 10.1002/3527604693.ch17

[7] Catalytic intermolecular amination of C-H bonds: Method development and mechanistic insights [J].

Fiori, Kristin Williams ;

Du Bois, J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (03) :562-568

[8] Intramolecular asymmetric amidations of sulfonamides and sulfamates catalyzed by chiral dirhodium(II) complexes [J].

Fruit, C ;

Müller, P .

HELVETICA CHIMICA ACTA, 2004, 87 (07) :1607-1615

[9] Mn(salen)-catalyzed enantioselective C-H amination [J].

Kohmura, Y ;

Katsuki, T .

TETRAHEDRON LETTERS, 2001, 42 (19) :3339-3342

[10] Toward a synthetically useful stereoselective C-H amination of hydrocarbons [J].

Liang, Chungen ;

Collet, Florence ;

Robert-Peillard, Fabien ;

Mueller, Paul ;

Dodd, Robert H. ;

Dauban, Philippe .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :343-350

← 1 2 3 →