Synthesis and evaluation of a broad range of new chiral phosphine-carbene ligands for asymmetric hydrogenation

被引：9

作者：

Passays, Johan ^{[1
,2
,3
]}

Ayad, Tahar ^{[4
]}

Ratovelomanana-Vidal, Virginie ^{[4
]}

Gaumont, Annie-Claude ^{[5
,6
]}

Jubault, Philippe ^{[1
,2
,3
]}

Leclerc, Eric ^{[1
,2
,3
]}

机构：

[1] INSA Rouen, F-76821 Mont St Aignan, France

[2] Univ Rouen, CNRS, UMR 6014, COBRA, F-76821 Mont St Aignan, France

[3] Univ Rouen, FR 3038, IRCOF, F-76821 Mont St Aignan, France

[4] Chim Paristech, Lab Charles Friedel, Ecole Natl Super Chim Paris, CNRS,UMR 7223, F-75231 Paris 05, France

[5] ENSICAEN, Lab Chim Mol & Thioorgan, CNRS, UMR 6507,INC3M,FR 3038, F-14050 Caen, France

[6] Univ Caen, F-14050 Caen, France

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 05期

关键词：

N-HETEROCYCLIC CARBENES; SUBSTITUTED BETA-AMIDOPHOSPHINES; PALLADIUM COMPLEXES; ENANTIOSELECTIVE HYDROGENATION; OLEFIN METATHESIS; IMIDAZOLIUM SALTS; NHC LIGANDS; CATALYSTS; CHEMISTRY; HYDROSILYLATION;

D O I：

10.1016/j.tetasy.2011.02.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A straightforward and gram scale synthesis (six-step synthesis from enantioenriched beta-hydroxy esters) of new structurally simple phosphine-carbene ligands bearing a single stereogenic centre has been achieved. Enantioselectivities of up to 60-63% could be achieved in the hydrogenation of methylstilbene and dehydroaminoacids when the reactions were performed under 20-50 bar hydrogen pressure. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：562 / 574

页数：13

共 69 条

[1] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[2] Looking for stable carbenes: The difficulty in starting anew [J].

Arduengo, AJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :913-921

[3] Asymmetric lithium(I) and copper(II) alkoxy-N-heterocyclic carbene complexes;: crystallographic characterisation and Lewis acid catalysis [J].

Arnold, PL ;

Rodden, M ;

Davis, KM ;

Scarisbrick, AC ;

Blake, AJ ;

Wilson, C .

CHEMICAL COMMUNICATIONS, 2004, (14) :1612-1613

[4] Synthesis and application of complexes of a novel chiral diphenylphosphino-functionalized N-heterocyclic carbene [J].

Bappert, E ;

Helmchen, G .

SYNLETT, 2004, (10) :1789-1793

[5] Synthesis and characterization of ruthenium(II) complexes containing chiral bis(ferrocenyl)-P-3 or -P2S ligands. Asymmetric transfer hydrogenation of acetophenone [J].

Barbaro, P ;

Bianchini, C ;

Togni, A .

ORGANOMETALLICS, 1997, 16 (13) :3004-3014

[6] Application of rhodium complexes of chiral diphenyl-phosphino-functionalized N-heterocyclic carbenes as catalysts in enantioselective conjugate additions of arylboronic acids [J].

Becht, JM ;

Bappert, E ;

Helmchen, G .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1495-1498

[7] Stereoselective chemoenzymatic synthesis of both enantiomers of protected 4-amino-2-pentanone [J].

Besse, P ;

Ciblat, S ;

Canet, JL ;

Troin, Y ;

Veschambre, H .

TETRAHEDRON-ASYMMETRY, 1999, 10 (11) :2213-2224

[8] Synthesis of new chiral N-heterocyclic carbene-imine ligands and their application to an asymmetric allylic alkylation reaction [J].

Bonnet, LG ;

Douthwaite, RE ;

Kariuki, BM .

ORGANOMETALLICS, 2003, 22 (21) :4187-4189

[9] Synthesis, structure and reactivity of palladium(II) complexes of chiral N-heterocyclic carbene-imine and -amine hybrid ligands [J].

Bonnet, LG ;

Douthwaite, RE ;

Hodgson, R ;

Houghton, J ;

Kariuki, BM ;

Simonovic, S .

DALTON TRANSACTIONS, 2004, (21) :3528-3535

[10] Expanding the medicinal chemistry toolbox: stereospecific generation of methyl group-containing propylene linkers [J].

Bosse, Kristopher ;

Marineau, Jason ;

Nason, Deane M. ;

Fliri, Anton J. ;

Segelstein, Barb E. ;

Desai, Kishor ;

Volkmann, Robert A. .

TETRAHEDRON LETTERS, 2006, 47 (41) :7285-7287

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