Preparation and application of polymer-grafted Ti-BINOL complexes as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes

被引：56

作者：

Yang, XW

Su, W

Liu, DX

Wang, HS

Shen, JH

Da, CS

Wang, R ^{[1
]}

Chan, ASC

机构：

[1] Lanzhou Univ, Sch Life Sci, Natl Lab Appl Organ Chem, Dept Biochem & Mol Biol, Lanzhou 730000, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Peoples R China

来源：

TETRAHEDRON | 2000年 / 56卷 / 22期

基金：

中国国家自然科学基金;

关键词：

Ti-BINOL complexes; enantioselective addition; aldehydes;

D O I：

10.1016/S0040-4020(00)00260-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomeric BINOL has been anchored to aminomethylated polystyrene resin at the 3- and 3,3'-positions of BINOL respectively. The resulting functionalized polymers 4 and 7 have been used as chiral ligands in the Ti-catalytic enantioselective addition of diethylzinc to aldehydes. Compared with the homogeneous ligands 5 and 8 in the same reaction, the polymer-supported ligands 4 and 6 gave, in some cases, higher enantioselectivity. The conformational inflexibility of the ligands was analyzed to illustrate the results. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3511 / 3516

页数：6

共 35 条

[1] Polymer-grafted Ti-TADDOL complexes. Preparation and use as catalysts in Diels-Alder reactions
Altava, B
Burguete, MI
Escuder, B
Luis, SV
Salvador, RV
Fraile, JM
Mayoral, JA
Royo, AJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) : 3126 - 3134
[2] Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst
Bayston, DJ
Travers, CB
Polywka, MEC
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (12) : 2015 - 2018
[3] Remarkable matrix effect in polymer-supported Jacobsen's alkene epoxidation catalysts
Canali, L
Cowan, E
Deleuze, H
Gibson, CL
Sherrington, DC
[J]. CHEMICAL COMMUNICATIONS, 1998, (23) : 2561 - 2562
[4] Novel spiro phosphinite ligands and their application in homogeneous catalytic hydrogenation reactions
Chan, ASC
Hu, WH
Pai, CC
Lau, CP
Jiang, YZ
Mi, AQ
Yan, M
Sun, J
Lou, RL
Deng, JG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) : 9570 - 9571
[5] Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes
Chan, ASC
Zhang, FY
Yip, CW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) : 4080 - 4081
[6] CHAN ASC, 1997, HUAXIE, V55, P117
[7] NOVEL ELECTRONIC EFFECTS OF REMOTE SUBSTITUENTS ON THE OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES
COREY, EJ
HELAL, CJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (50) : 9153 - 9156
[8] CHANGES OF ENANTIOSELECTIVITY WITH THE SUBSTRATE RATIO FOR THE ADDITION OF DIETHYLZINC TO ALDEHYDES USING A CATALYST COUPLED TO A SOLUBLE POLYMER
DREISBACH, C
WISCHNEWSKI, G
KRAGL, U
WANDREY, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (07): : 875 - 878
[9] Organic synthesis on soluble polymer supports: Liquid-phase methodologies
Gravert, DJ
Janda, KD
[J]. CHEMICAL REVIEWS, 1997, 97 (02) : 489 - 509
[10] Halm C, 1998, ANGEW CHEM INT EDIT, V37, P510, DOI 10.1002/(SICI)1521-3773(19980302)37:4<510::AID-ANIE510>3.0.CO

← 1 2 3 4 →