Immobilization of asymmetric multifunctional catalysts on an insoluble polymer

被引：76

作者：

Matsunaga, S ^{[1
]}

Ohshima, T ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 44期

基金：

日本学术振兴会;

关键词：

asymmetric catalyst; asymmetric synthesis; solid-phase synthesis; Michael reaction; linked-BINOL;

D O I：

10.1016/S0040-4039(00)01486-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polymer-supported linked-BINOL was synthesized to immobilize asymmetric catalysts with two BINOL units. The advantage of the polymer-supported linked-BINOL over randomly polymer-supported BINOL was confirmed by asymmetric Michael reaction. A novel polymer-supported La-Zn-linked-BINOL complex afforded the Michael adduct in good yield and moderate ee. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8473 / 8478

页数：6

共 19 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] 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 diaqua and hydroxo complexes with polymer-supported BINAP ligands and their use for catalytic enantioselective reactions [J].

Fujii, A ;

Sodeoka, M .

TETRAHEDRON LETTERS, 1999, 40 (45) :8011-8014

[4]

Heckel A, 2000, ANGEW CHEM INT EDIT, V39, P163, DOI 10.1002/(SICI)1521-3773(20000103)39:1<163::AID-ANIE163>3.0.CO

[5]

2-J

[6] Development of highly enantioselective polymeric catalysts using rigid and sterically regular chiral polybinaphthols [J].

Huang, WS ;

Hu, QS ;

Zheng, XF ;

Anderson, J ;

Pu, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4313-4314

[7] Hetero-dinuclear metal complexes for RNA hydrolysis [J].

Kamitani, J ;

Kawahara, R ;

Yashiro, M ;

Komiyama, M .

CHEMISTRY LETTERS, 1998, (10) :1047-1048

[8] Stable, storable, and reusable asymmetric catalyst: A novel La-linked-BINOL complex for the catalytic asymmetric Michael reaction [J].

Kim, YS ;

Matsunaga, S ;

Das, J ;

Sekine, A ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) :6506-6507

[9] Chiral catalyst optimization using both solid-phase and liquid-phase methods in asymmetric aza Diels-Alder reactions [J].

Kobayashi, S ;

Kusakabe, K ;

Ishitani, H .

ORGANIC LETTERS, 2000, 2 (09) :1225-1227

[10] Catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile promoted by gallium heterobimetallic multifunctional complexes [J].

Matsunaga, S ;

Das, J ;

Roels, J ;

Vogl, EM ;

Yamamoto, N ;

Iida, T ;

Yamaguchi, K ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2252-2260

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