Asymmetric allylic substitution catalyzed by palladium-Yliphos complex

被引:30
作者
Ohta, T [1 ]
Sasayama, H [1 ]
Nakajima, O [1 ]
Kurahashi, N [1 ]
Fujii, T [1 ]
Furukawa, I [1 ]
机构
[1] Doshisha Univ, Fac Engn, Dept Mol Sci & Technol, Kyoto 6100394, Japan
关键词
D O I
10.1016/S0957-4166(03)00046-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Allylic substitution reactions catalyzed by Pd- or Pt-Yliphos complexes are examined. The reaction of 1,3-diphenyl-2-propenyl acetate with benzylamine proceeded in the presence of Pd(dba)(2)-Yliphos to give N-benzyl-1,3-diphenyl-2-propenylamine in high yields with high enantioselectivities (up to 90% ee). Furthermore, the allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate catalyzed by Pd-Yliphos complex resulted in high enantioselectivity (95% ee) in the presence of LiH as base. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:537 / 542
页数:6
相关论文
共 34 条
[1]   Sulfur-imine mixed donor chelate ligands for asymmetric catalysis: enantioselective allylic alkylation [J].
Anderson, JC ;
James, DS ;
Mathias, JP .
TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :753-756
[2]   ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES [J].
AUBURN, PR ;
MACKENZIE, PB ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2033-2046
[3]   ALPHA-AMINO ESTER DERIVATIVES AS NUCLEOPHILES IN STEREOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS [J].
BALDWIN, IC ;
WILLIAMS, JMJ ;
BECKETT, RP .
TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1515-1518
[4]  
BOSNICH B, 1981, TOP STEREOCHEM, V12, P119
[5]   MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].
BROWN, JM ;
HULMES, DI ;
GUIRY, PJ .
TETRAHEDRON, 1994, 50 (15) :4493-4506
[6]   Synthesis of homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane: Use in asymmetric catalysis [J].
Chelucci, G ;
Cabras, MA ;
Botteghi, C ;
Basoli, C ;
Marchetti, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :885-895
[7]   PREPARATION OF PLATINUM PI-OLEFIN COMPLEXES FROM BIS(1,5-DIPHENYLPENTA-1,4-DIEN-3-ONE)PLATINUM(0) [J].
CHERWINSKI, WJ ;
JOHNSON, BFG ;
LEWIS, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (13) :1405-1409
[8]   Enantioselective allylic substitution using a novel (phosphino-1,3-oxazine)palladium catalyst [J].
Evans, PA ;
Brandt, TA .
TETRAHEDRON LETTERS, 1996, 37 (51) :9143-9146
[9]   Et2Zn as a base:: zinc enolate free from other metals significantly enhances the enantiomeric excess in palladium-catalyzed allylic alkylation [J].
Fuji, K ;
Kinoshita, N ;
Tanaka, K .
CHEMICAL COMMUNICATIONS, 1999, (18) :1895-1896
[10]   Retention of regiochemistry of allylic esters in palladium-catalyzed allylic alkylation in the presence of a MOP ligand [J].
Hayashi, T ;
Kawatsura, M ;
Uozumi, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1681-1687