Palladium-catalyzed asymmetric allylic substitution in aqueous media using amphiphilic resin-supported MOP ligands

被引：113

作者：

Uozumi, Y ^{[1
]}

Danjo, H

Hayashi, T

机构：

[1] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

[2] Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 45期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4039(98)01812-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of amphiphilic resin-supported MOP ligands PEP-MOP were prepared on a polyethylene glycol-polystyrene graft copolymer. Palladium complexes of EP-MOP were found to be effective as catalysts for the asymmetric substitution of 1,3-diphenyl-2-propenyl acetate with 3-methyl-2,4-pentanedione in aqueous K2CO3 to give 1,3-diphenyl-4-acetyl-4-methyl-1-hexen-5-one of up to 81% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8303 / 8306

页数：4

共 28 条

[1] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE [J].

AMATORE, C ;

BLART, E ;

GENET, JP ;

JUTAND, A ;

LEMAIREAUDOIRE, S ;

SAVIGNAC, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6829-6839

[2] Preparation and use of a polymer supported BINAP hydrogenation catalyst [J].

Bayston, DJ ;

Fraser, JL ;

Ashton, MR ;

Baxter, AD ;

Polywka, MEC ;

Moses, E .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :3137-3140

[3] PALLADIUM(0)-CATALYZED SUBSTITUTION OF ALLYLIC SUBSTRATES IN AN AQUEOUS-ORGANIC MEDIUM [J].

BLART, E ;

GENET, JP ;

SAFI, M ;

SAVIGNAC, M ;

SINOU, D .

TETRAHEDRON, 1994, 50 (02) :505-514

[4] PALLADIUM-CATALYZED ARYLATION OF STYRENE AND ACRYLIC-ACID IN WATER [J].

BUMAGIN, NA ;

BYKOV, VV ;

SUKHOMLINOVA, LI ;

TOLSTAYA, TP ;

BELETSKAYA, IP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 486 (1-2) :259-262

[5]

BUNIN BA, 1998, COMBINATORIAL INDEX

[6] ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].

CONSIGLIO, G ;

WAYMOUTH, RM .

CHEMICAL REVIEWS, 1989, 89 (01) :257-276

[7]

GENET JP, 1992, SYNLETT, P715

[8] PRACTICAL PALLADIUM-MEDIATED DEPROTECTIVE METHOD OF ALLYLOXYCARBONYL IN AQUEOUS-MEDIA [J].

GENET, JP ;

BLART, E ;

SAVIGNAC, M ;

LEMEUNE, S ;

LEMAIREAUDOIRE, S ;

PARIS, JM ;

BERNARD, JM .

TETRAHEDRON, 1994, 50 (02) :497-503

[9] PALLADIUM-CATALYZED REACTIONS IN AQUEOUS-MEDIA - AN EFFICIENT REMOVAL OF ALLYLOXYCARBONYL PROTECTING GROUP FROM OXYGEN AND NITROGEN [J].

GENET, JP ;

BLART, E ;

SAVIGNAC, M ;

LEMEUNE, S ;

PARIS, JM .

TETRAHEDRON LETTERS, 1993, 34 (26) :4189-4192

[10] The combinatorial synthesis of chiral phosphine ligands [J].

Gilbertson, SR ;

Wang, XF .

TETRAHEDRON LETTERS, 1996, 37 (36) :6475-6478

← 1 2 3 →