Synthesis of a new class of conformationally rigid phosphino-oxazolines: Highly enantioselective ligands for Ir-catalyzed asymmetric hydrogenation

被引:82
作者
Liu, D [1 ]
Tang, WJ [1 ]
Zhang, X [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
关键词
D O I
10.1021/ol0362717
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of conformationally rigid phosphino-oxazoline ligands were synthesized from readily available enantiopure phenyl glycinol. Ir complexes with these ligands are air-stable and highly enantioselective catalysts for asymmetric hydrogenation of aryl alkenes and alpha,beta-unsaturated esters in up to 99% ee.
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页码:513 / 516
页数:4
相关论文
共 35 条
[1]   Novel P,N ligands derived from (R)- and (S)-1-phenylethylamine with (2R,5R)-2,5-dimethylphospholanyl groups (DuPHAMIN) for asymmetric catalysis [J].
Brauer, DJ ;
Kottsieper, KW ;
Rossenbach, S ;
Stelzer, O .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (09) :1748-1755
[2]  
Brown J. M., 1983, HOMOGENEOUS CATALYSI, P137
[3]   New P,N Ligands for asymmetric Ir-catalyzed reactions [J].
Bunlaksananusorn, T ;
Polborn, K ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (33) :3941-3943
[4]   SILYLAMINES IN ORGANIC-SYNTHESIS - PREPARATION AND SOME REACTIONS OF N,C-DILITHIOSILYLAMINES [J].
BURNS, SA ;
CORRIU, RJP ;
HUYNH, V ;
MOREAU, JJE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 333 (03) :281-290
[5]   IRIDIUM COMPOUNDS IN CATALYSIS [J].
CRABTREE, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (09) :331-338
[6]   A conformational toolbox of oxazoline ligands. [J].
Davies, IW ;
Gerena, L ;
Cai, DW ;
Larsen, RD ;
Verhoeven, TR ;
Reider, PJ .
TETRAHEDRON LETTERS, 1997, 38 (07) :1145-1148
[7]   BIS(IMINE)-COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACID CATALYSTS FOR THE DIELS-ALDER REACTION [J].
EVANS, DA ;
LECTKA, T ;
MILLER, SJ .
TETRAHEDRON LETTERS, 1993, 34 (44) :7027-7030
[8]   Asymmetric hydrogenation of α-ethylstyrenes catalyzed by chiral ruthenium complexes [J].
Forman, GS ;
Ohkuma, T ;
Hems, WP ;
Noyori, R .
TETRAHEDRON LETTERS, 2000, 41 (49) :9471-9475
[9]   Baker's yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (-)-curcuquinone and (+)-curcuhydroquinone [J].
Fuganti, C ;
Serra, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (22) :3758-3764
[10]   Baker's yeast mediated enantioselective synthesis of the bisabolane sesquiterpenes curcumene, turmerone, dehydrocurcumene and nuciferal [J].
Fuganti, C ;
Serra, S ;
Dulio, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (03) :279-282