Catalytic asymmetric addition of alkynylzinc reagents to ketones using polymer-supported chiral Schiff-base amino alcohols

被引：28

作者：

Chen, Chao ^{[1
,2
]}

Hong, Liang ^{[1
]}

Zhang, Bangzhi ^{[1
]}

Wang, Rui ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China

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

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 02期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetasy.2007.11.040

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Polymer-supported Schiff-base of optically active amino alcohols was used as chiral ligands in the enantioselective addition of alkynylzinc to simple ketones. At a 10 mol % ligand loading, chiral propargylic alcohols with moderate to good ee values (up to 89%) were produced. The polymeric catalyst could be recycled many times and used for further reactions. (C) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：191 / +

页数：8

相关论文

共 65 条

[1] Best design of heterogenized β-aminoalcohols for improvement of enantioselective addition of diethylzinc to benzaldehyde [J].

Abramson, S ;

Laspéras, M ;

Galarneau, A ;

Desplantier-Giscard, D ;

Brunel, D .

CHEMICAL COMMUNICATIONS, 2000, (18) :1773-1774

[2] Polymer-grafted Ti-TADDOL complexes. Preparation and use as catalysts in Diels-Alder reactions [J].

Altava, B ;

Burguete, MI ;

Escuder, B ;

Luis, SV ;

Salvador, RV ;

Fraile, JM ;

Mayoral, JA ;

Royo, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3126-3134

[3] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].

Anand, NK ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688

[4] Effect of spacers on the activity of soluble polymer supported catalysts for the asymmetric addition of diethylzinc to aldehydes [J].

Anyanwu, UK ;

Venkataraman, D .

TETRAHEDRON LETTERS, 2003, 44 (34) :6445-6448

[5] Factors affecting the efficiency of hybrid chiral mesoporous silicas used as heterogeneous inorganic-organic catalysts in the enantioselective alkylation of benzaldehyde [J].

Bellocq, N ;

Abramson, S ;

Laspéras, M ;

Brunel, D ;

Moreau, P .

TETRAHEDRON-ASYMMETRY, 1999, 10 (16) :3229-3241

[6] Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions [J].

Boyall, D ;

Frantz, DE ;

Carreira, EM .

ORGANIC LETTERS, 2002, 4 (15) :2605-2606

[7] A new type of ligand derived from N-terminal protected dipeptides in enantioselective addition of phenylacetylene to aromatic ketones at room temperature [J].

Cai, Hua-qing ;

Chen, Chao ;

Liu, Lei ;

Ni, Jing-man ;

Wang, Rui .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) :86-91

[8] Polystyrene-supported amino alcohol ligands for the heterogeneous asymmetric addition of phenyl zinc reagents to aldehydes [J].

Castellnou, D ;

Fontes, M ;

Jimeno, C ;

Font, D ;

Solà, L ;

Verdaguer, X ;

Pericàs, MA .

TETRAHEDRON, 2005, 61 (51) :12111-12120

[9] Polystyrene-supported (R)-2-piperazino-1,1,2-triphenylethanol:: A readily available supported ligand with unparalleled catalytic activity and enantioselectivity [J].

Castellnou, D ;

Solà, L ;

Jimeno, C ;

Fraile, JM ;

Mayoral, JA ;

Riera, A ;

Pericàs, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :433-438

[10] Low ligand loading, highly enantioselective addition of phenylacetylene to aromatic ketones catalyzed by Schiff-base amino alcohols [J].

Chen, Chao ;

Hong, Liang ;

Xu, Zhao-Qing ;

Liu, Lei ;

Wang, Rui .

ORGANIC LETTERS, 2006, 8 (11) :2277-2280

← 1 2 3 4 5 6 7 →