A new ligand containing a unique combination of backbone- and P-centered chirality:: synthesis, resolution and asymmetric catalysis using a chiral enantiopure 2,2′-biphospholene

被引:25
作者
Bienewald, F [1 ]
Ricard, L [1 ]
Mercier, F [1 ]
Mathey, F [1 ]
机构
[1] Ecole Polytech, DCPH, Lab Heteroelements & Coordinat, CNRS,UMR 7633, F-91128 Palaiseau, France
关键词
D O I
10.1016/S0957-4166(99)00547-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiopure 2,2'-bi(1-phenyl-3,4-dimethyl-2,5-dihydro-1H-phosphole) has been synthesized and tested in the rhodium-catalyzed asymmetric hydrogenation of alpha-acetamidocinnamic acid. Enantioselectivities up to 75% have been achieved. The absolute configuration of the biphospholene was determined by X-ray diffraction methods on a crystalline tungsten carbonyl derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.
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收藏
页码:4701 / 4707
页数:7
相关论文
共 21 条
[1]   C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519
[2]   NEW ELECTRON-RICH CHIRAL PHOSPHINES FOR ASYMMETRIC CATALYSIS [J].
BURK, MJ ;
FEASTER, JE ;
HARLOW, RL .
ORGANOMETALLICS, 1990, 9 (10) :2653-2655
[3]   ASYMMETRIC SYNTHESIS OF HYDRATROPIC ACID AND AMINO-ACIDS BY HOMOGENEOUS CATALYTIC HYDROGENATION [J].
DANG, TP ;
KAGAN, HB .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (10) :481-&
[4]  
Deschamps E, 1991, Heteroat. Chem., V2, P377
[5]  
Eliel E.L., 1994, Stereochemistry of Organic Compounds
[6]   Optical resolution, configurational stability, and coordination chemistry of the P-chiral heterocyclic diphosphine 1,1′-diphenyl-3,3′,4,4′-tetramethyl-2,2′-diphosphole-3,3′-diene [J].
He, GS ;
Mok, KF ;
Leung, PH .
ORGANOMETALLICS, 1999, 18 (20) :4027-4031
[7]  
JOHNSON BFG, 1969, J AM CHEM SOC, V91, P5187
[9]   ASYMMETRIC HYDROGENATION WITH A COMPLEX OF RHODIUM AND A CHIRAL BISPHOSPHINE [J].
KNOWLES, WS ;
SABACKY, MJ ;
VINEYARD, BD ;
WEINKAUFF, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (09) :2567-2568
[10]   NICKEL-PROMOTED THERMAL DIMERIZATION OF 1-PHENYL-3,4-DIMETHYLPHOSPHOLE - THE 1ST SYNTHESIS OF A DIPHOSPHOLENE [J].
MERCIER, F ;
MATHEY, F ;
FISCHER, J ;
NELSON, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :425-426