Chiral calix[4]arene-based diphosphites as ligands in the asymmetric hydrogenation of prochiral olefins

被引：36

作者：

Marson, Angelica

Freixa, Zoraida

Kamer, Paul C. J.

van Leeuwen, Piet W. N. M. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[3] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WV Amsterdam, Netherlands

来源：

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY | 2007年 / 29期

关键词：

homogeneous catalysis; stereoselective catalysis; asymmetric hydrogenation; calixarenes; diphosphites;

D O I：

10.1002/ejic.200700764

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral calixarene-based diphosphite ligands 3a-d have been obtained via lower-rim functionalisation of the p-tert-butylcalix[4]arene core. High enantiomeric excesses (up to 94 %) and good activities were obtained in the rhodium-catalyzed asymmetric hydrogenation of prochiral olefins with TADDOL-containing diphosphites 3c,d. This is the first example of chiral calix[4]arene-modified ligands that induce high enantioselectivity in metal-catalysed asymmetric reactions.

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页码：4587 / 4591

页数：5

相关论文

共 46 条

[1] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL [J].

Alexakis, A ;

Vastra, J ;

Burton, J ;

Benhaim, C ;

Mangeney, P .

TETRAHEDRON LETTERS, 1998, 39 (43) :7869-7872

[2]

[Anonymous], 2005, HDB CHIRAL CHEM

[3]

[Anonymous], ANGEW CHEM

[4] CHELATING DIPHOSPHITE COMPLEXES OF NICKEL(0) AND PLATINUM(0) - THEIR REMARKABLE STABILITY AND HYDROCYANATION ACTIVITY [J].

BAKER, MJ ;

HARRISON, KN ;

ORPEN, AG ;

PRINGLE, PG ;

SHAW, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (12) :803-804

[5] The economic use of precious chiral diphosphine ligands-DuPHOS and its rhodium(I) COD and NBD complexes [J].

Börner, A ;

Heller, D .

TETRAHEDRON LETTERS, 2001, 42 (02) :223-225

[6] Fluxional processes in asymmetric hydroformylation catalysts [HRhL-L(CO)2] containing C2-symmetric diphosphite ligands [J].

Buisman, GJH ;

van der Veen, LA ;

Kamer, PCJ ;

van Leeuwen, PWNM .

ORGANOMETALLICS, 1997, 16 (26) :5681-5687

[7] Chiral cooperativity in diastereomeric diphosphite ligands: Effects on the rhodium-catalyzed enantioselective hydroformylation of styrene [J].

Buisman, GJH ;

vanderVeen, LA ;

Klootwijk, A ;

deLange, WGJ ;

Kamer, PCJ ;

vanLeeuwen, PWNM ;

Vogt, D .

ORGANOMETALLICS, 1997, 16 (13) :2929-2939

[8] Rhodium(I) complexes of robust phosphites derived from calix[4]arenes and their application in the hydroformylation of 1-hexene [J].

Cobley, CJ ;

Ellis, DD ;

Orpen, AG ;

Pringle, PG .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (07) :1109-1112

[9] On the economic application of DuPHOS rhodium(I) catalysts: a comparison of COD versus NBD precatalysts [J].

Cobley, CJ ;

Lennon, IC ;

McCague, R ;

Ramsden, JA ;

Zanotti-Gerosa, A .

TETRAHEDRON LETTERS, 2001, 42 (42) :7481-7483

[10] Chiral diphosphites derived from D-glucose:: New highly modular ligands for the asymmetric catalytic hydrogenation [J].

Diéguez, M ;

Ruiz, A ;

Claver, C .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3796-3801

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