PS-PEG resin-supported palladium-MOP complexes.: Application in asymmetric π-allylic reduction

被引:30
作者
Hocke, H [1 ]
Uozumi, Y [1 ]
机构
[1] IMS, Okazaki, Aichi 4448787, Japan
基金
日本科学技术振兴机构; 日本学术振兴会;
关键词
MOP; immobilized recyclable catalysts; asymmetric catalysis; pi-allylic reduction;
D O I
10.1016/j.tet.2004.07.093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homochiral palladium complexes of polymeric 2'-, 6-, and 6'-anchored 2-diphenylphosphino-1,1'-binaphthyl (MOP) ligands were prepared on polystyrene-poly(ethylene glycol) (PS-PEG) resin. The PS-PEG resin-supported palladium-MOP complexes exhibited high catalytic activity, stereoselectivity (up to 80% ee), and recyclability (six times) in the asymmetric allylic reduction of 1-vinyl-1,2,3,4-tetrahydronaphth-1-yl benzoate to give 1-vinyl-1,2,3,4-tetrahydronaphthalene. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9297 / 9306
页数:10
相关论文
共 70 条
[51]  
2-I
[52]   Polymer-supported C2-symmetric ligands for palladium-catalyzed asymmetric allylic alkylation reactions [J].
Trost, BM ;
Pan, ZY ;
Zambrano, J ;
Kujat, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4691-4693
[53]   Heck reaction in water with amphiphilic resin-supported palladium-phosphine complexes [J].
Uozumi, Y ;
Kimura, T .
SYNLETT, 2002, (12) :2045-2048
[54]   Asymmetric allylic amination in water catalyzed by an amphiphilic resin-supported chiral palladium complex [J].
Uozumi, Y ;
Tanaka, H ;
Shibatomi, K .
ORGANIC LETTERS, 2004, 6 (02) :281-283
[55]   The Sonogashira reaction in water via an amphiphilic resin-supported palladium-phosphine complex under copper-free conditions [J].
Uozumi, Y ;
Kobayashi, Y .
HETEROCYCLES, 2003, 59 (01) :71-74
[56]   An amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water [J].
Uozumi, Y ;
Nakai, Y .
ORGANIC LETTERS, 2002, 4 (17) :2997-3000
[57]   Green catalysis: Hydroxycarbonylation of aryl halides in water catalyzed by an amphiphilic resin-supported phosphine-palladium complex [J].
Uozumi, Y ;
Watanabe, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6921-6923
[58]   Catalytic asymmetric allylic alkylation in water with a recyclable amphiphilic resin-supported P,N-chelating palladium complex [J].
Uozumi, Y ;
Shibatomi, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2919-2920
[59]   New amphiphilic palladium-phosphine complexes bound to solid supports: Preparation and use for catalytic allylic substitution in aqueous media [J].
Uozumi, Y ;
Danjo, H ;
Hayashi, T .
TETRAHEDRON LETTERS, 1997, 38 (20) :3557-3560
[60]   Cross-coupling of aryl halides and allyl acetates with arylboron reagents in water using an amphiphilic resin-supported palladium catalyst [J].
Uozumi, Y ;
Danjo, H ;
Hayashi, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3384-3388