Assembled catalysts of titanium and non-cross-linked chiral copolymers for an enantioselective carbonyl-ene reaction

被引：41

作者：

Yamada, YMA ^{[1
]}

Ichinohe, M ^{[1
]}

Takahashi, H ^{[1
]}

Ikegami, S ^{[1
]}

机构：

[1] Teikyo Univ, Fac Pharmaceut Sci, Kanagawa 1990195, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 18期

关键词：

asymmetric reactions; ene reactions; polymer support; self-assembly; titanium and compounds;

D O I：

10.1016/S0040-4039(02)00427-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New insoluble chiral catalysts were prepared from a self-assembly of Ti(O-i-Pr)(4) and non-cross-linked copolymers with (R)-binaphthol (BINOL) pendant groups. In the presence of one of the chiral catalysts, an enantioselective carbonyl-ene reaction proceeded at room temperature to give an adduct in 85% yield with 88% ee. This insoluble assembled catalyst was easily prepared and reusable. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3431 / 3434

页数：4

共 30 条

[1] Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides [J].

Annis, DA ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4147-4154

[2] Poly(ethylene glycol)-supported bisoxazolines as ligands for catalytic enantioselective synthesis [J].

Annunziata, R ;

Benaglia, M ;

Cinquini, M ;

Cozzi, F ;

Pitillo, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3160-3166

[3] Immobilization of heterobimetallic multifunctional asymmetric catalyst [J].

Arai, T ;

Hu, QS ;

Zheng, XF ;

Pu, L ;

Sasai, H .

ORGANIC LETTERS, 2000, 2 (26) :4261-4263

[4] 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

[5] Self-organization of ligands in multi-component titanium catalysts for the enantioselective ene reaction of glyoxylates [J].

Chavarot, M ;

Byrne, JJ ;

Chavant, PY ;

Pardillos-Guindet, J ;

Vallée, Y .

TETRAHEDRON-ASYMMETRY, 1998, 9 (21) :3889-3894

[6] Immobilization of chiral ligands on polymer fibers by electron beam induced grafting and applications in enantioselective catalysis [J].

Degni, S ;

Wilén, CE ;

Leino, R .

ORGANIC LETTERS, 2001, 3 (16) :2551-2554

[7] C2-symmetric copper(II) complexes as chiral Lewis acids.: Catalytic enantioselective carbonyl-ene reactions with glyoxylate and pyruvate esters [J].

Evans, DA ;

Tregay, SW ;

Burgey, CS ;

Paras, NA ;

Vojkovsky, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7936-7943

[8]

Fodor K, 1999, ENANTIOMER, V4, P497

[9] Asymmetric catalysis on sequentially-linked columns [J].

Hafez, AM ;

Taggi, AE ;

Dudding, T ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10853-10859

[10] Synthesis and catalytic applications of soluble polymer-supported BINOL [J].

Jayaprakash, D ;

Sasai, H .

TETRAHEDRON-ASYMMETRY, 2001, 12 (18) :2589-2595

← 1 2 3 →