Ligand-assisted, copper-catalyzed enantioselective benzylic amination

被引：20

作者：

Barman, Dipti N. ^{[1
]}

Nicholas, Kenneth M. ^{[1
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 14期

基金：

美国国家科学基金会;

关键词：

Hydrocarbon amination; Ligand-assisted copper catalysis; Enantioselective; Chloramine-T; C-H BONDS; INTERMOLECULAR AMINATION; CHIRAL CATALYSTS; AMIDATION; AZIRIDINATION; COMPLEXES; DIRHODIUM(II); HYDROCARBONS; ALLYLATION; PORPHYRINS;

D O I：

10.1016/j.tetlet.2010.01.118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several classes of ligands, including alpha-amino acids, diamines, diphosphines, bis-oxazolines, and diimines, support efficient copper-catalyzed amination of benzylic hydrocarbons by anhydrous chloramine-T. Catalysts derived from homochiral ligands, particularly chiral diimines, effect aminosulfonation with low to moderate enantioselectivity. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1815 / 1818

页数：4

共 51 条

[1] Schiff Bases as Potential Fungicides and Nitrification Inhibitors [J].

Aggarwal, Nisha ;

Kumar, Rajesh ;

Dureja, Prem ;

Rawat, Diwan S. .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (18) :8520-8525

[2] A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T trihydrate [J].

Albone, DP ;

Aujla, PS ;

Taylor, PC ;

Challenger, S ;

Derrick, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9569-9571

[3] Copper-Nitrene Complexes in Catalytic C-H Amination [J].

Badiei, Yosra M. ;

Dinescu, Adriana ;

Dai, Xiliang ;

Palomino, Robert M. ;

Heinemann, Frank W. ;

Cundari, Thomas R. ;

Warren, Timothy H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (51) :9961-9964

[4] Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T [J].

Bhuyan, Ranjana ;

Nicholas, Kenneth M. .

ORGANIC LETTERS, 2007, 9 (20) :3957-3959

[5] Chiral hybrid silica:: sol-gel heterogenisation of trans-(1R,2R)-diaminocyclohexane ligands for the rhodium catalysed enantioselective reduction of acetophenone [J].

Brethon, A ;

Moreau, JJE ;

Man, MWC .

TETRAHEDRON-ASYMMETRY, 2004, 15 (03) :495-502

[6] Catalytic amination reactions mediated by Co(II) Schiff base complexes [J].

Caselli, A ;

Gallo, E ;

Ragaini, F ;

Oppezzo, A ;

Cenini, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (08) :2142-2148

[7] Catalytic C-H amination: recent progress and future directions [J].

Collet, Florence ;

Dodd, Robert H. ;

Dauban, Philippe .

CHEMICAL COMMUNICATIONS, 2009, (34) :5061-5074

[8] Catalytic, enantioselective allylation of α-iminoesters promoted by silver(I) complexes of chiral imines [J].

Colombo, Federica ;

Annunziata, Rita ;

Benaglia, Maurizio .

TETRAHEDRON LETTERS, 2007, 48 (15) :2687-2690

[9] Recent advances in catalytic intramolecular C-H aminations [J].

Davies, HML ;

Long, MS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3518-3520

[10] Expanding the scope of C-H amination through catalyst design [J].

Espino, CG ;

Fiori, KW ;

Kim, M ;

Du Bois, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15378-15379

← 1 2 3 4 5 6 →