Synthesis of new bicyclic P-N ligands and their application in asymmetric Pd-catalyzed π-allyl alkylation and Heck reaction

被引:81
作者
Gilbertson, SR
Genov, DG
Rheingold, AL
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63170 USA
[2] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA
关键词
D O I
10.1021/ol006323h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of phosphine oxazoline ligands based on P-chiral 1-phosphanorbornadienes is reported. The use of these ligands in palladium catalyzed asymmetric allylation and Heck reaction is described.
引用
收藏
页码:2885 / 2888
页数:4
相关论文
共 30 条
[21]   PALLADIUM-CATALYZED ASYMMETRIC ALKENYLATION OF CYCLIC OLEFINS [J].
OZAWA, F ;
KOBATAKE, Y ;
HAYASHI, T .
TETRAHEDRON LETTERS, 1993, 34 (15) :2505-2508
[22]   Design of chiral ligands for asymmetric catalysis: From C-2-symmetric semicorrins and bisoxazolines to non-symmetric phosphinooxazolines [J].
Pfaltz, A .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (03) :189-194
[23]   PREPARATION OF SCALEMIC P-CHIRAL PHOSPHINES AND THEIR DERIVATIVES [J].
PIETRUSIEWICZ, KM ;
ZABLOCKA, M .
CHEMICAL REVIEWS, 1994, 94 (05) :1375-1411
[24]   BIPNOR: A new, efficient bisphosphine having two chiral, nonracemizable, bridgehead phosphorus centers for use in asymmetric catalysis [J].
Robin, F ;
Mercier, F ;
Ricard, L ;
Mathey, F ;
Spagnol, M .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (08) :1365-1369
[25]   CATALYTIC ASYMMETRIC-SYNTHESIS BY MEANS OF SECONDARY INTERACTION BETWEEN CHIRAL LIGANDS AND SUBSTRATES [J].
SAWAMURA, M ;
ITO, Y .
CHEMICAL REVIEWS, 1992, 92 (05) :857-871
[26]   CATALYSIS OF ALLYLIC SUBSTITUTIONS BY PD COMPLEXES OF OXAZOLINES CONTAINING AN ADDITIONAL P, S, OR SE CENTER - X-RAY CRYSTAL-STRUCTURES AND SOLUTION STRUCTURES OF CHIRAL PI-ALLYL PALLADIUM COMPLEXES OF PHOSPHINOARYLOXAZOLINES [J].
SPRINZ, J ;
KIEFER, M ;
HELMCHEN, G ;
HUTTNER, G ;
WALTER, O ;
ZSOLNAI, L ;
REGGELIN, M .
TETRAHEDRON LETTERS, 1994, 35 (10) :1523-1526
[27]   A MODULAR APPROACH FOR LIGAND DESIGN FOR ASYMMETRIC ALLYLIC ALKYLATIONS VIA ENANTIOSELECTIVE PALLADIUM-CATALYZED IONIZATIONS [J].
TROST, BM ;
VANVRANKEN, DL ;
BINGEL, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9327-9343
[28]  
VALENTINE DJ, 1984, ASYMMETRIC SYNTHESIS, V4
[29]  
WASCHBUSCH K, 1995, B SOC CHIM FR, V132, P910
[30]   A direct synthesis of P-chiral phosphine boranes via dynamic resolution of lithiated racemic tert-butylphenylphosphine-borane with (-)-sparteine [J].
Wolfe, B ;
Livinghouse, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (20) :5116-5117