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
[1]  
BREQUE A, 1989, NEW J CHEM, V13, P369
[2]   PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
NUGENT, WA ;
HARLOW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138
[3]   PROTON [1,5] SHIFTS IN P-UNSUBSTITUTED 1H-PHOSPHOLES - SYNTHESIS AND CHEMISTRY OF 2H-PHOSPHOLE DIMERS [J].
CHARRIER, C ;
BONNARD, H ;
DELAUZON, G ;
MATHEY, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) :6871-6877
[4]   ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].
DAWSON, GJ ;
FROST, CG ;
WILLIAMS, JMJ .
TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150
[5]   ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].
FARINA, V ;
KAPADIA, S ;
KRISHNAN, B ;
WANG, CJ ;
LIEBESKIND, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5905-5911
[6]   A straightforward access to alpha-functional phospholide ions [J].
Holand, S ;
Jeanjean, M ;
Mathey, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :98-100
[7]   P-chiral bis(trialkylphosphine) ligands and their use in highly enantioselective hydrogenation reactions [J].
Imamoto, T ;
Watanabe, J ;
Wada, Y ;
Masuda, H ;
Yamada, H ;
Tsuruta, H ;
Matsukawa, S ;
Yamaguchi, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1635-1636
[8]  
Imamoto T., 1992, HDB ORGANOPHOSPHORUS
[9]  
Kagan H.B., 1990, CHEM ORGANOPHOSPHORU, V1
[10]  
Kudis S, 1998, ANGEW CHEM INT EDIT, V37, P3047, DOI 10.1002/(SICI)1521-3773(19981116)37:21<3047::AID-ANIE3047>3.0.CO