Synthesis of a polymer(fiber)-supported chiral amino alcohol and its application to enantioselective addition of diethylzinc to benzaldehyde

被引:0
作者
Lin, Kun-Hua [1 ]
Zeng, Qing-Bin
Li, Ming-Xing
Pan, Qing-Yi
Song, Mao-Ping
Wu, Yang-Jie
机构
[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
[2] Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Peoples R China
关键词
polymer(fiber)-supported chiral amino alcohol; diethylzinc; benzaldehyde; enantioselective addition;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A polymer(fiber)-supported chiral amino alcohol was synthesized and applied to the enantioselective addition of diethylzinc to benzaldehyde. Compared with the resin-supported chiral amino alcohol in the same reactive time, the fiber-supported amino alcohol could increase the yield and ee value by 34% and 9% respectively. This fiber-supported catalyst could be recycled more than 5 times. The reason why catalytic property was dropped down in recycle was proved to be the loss of catalyst by the analysis of their SEM photographs.
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收藏
页码:718 / 722
页数:5
相关论文
共 23 条
[1]   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
[2]   New supported β-amino alcohols as efficient catalysts for the enantioselective addition of diethylzinc to benzaldehyde under flow conditions [J].
Burguete, MI ;
García-Verdugo, E ;
Vicent, MJ ;
Luis, SV ;
Pennemann, H ;
von Keyserling, NG ;
Martens, J .
ORGANIC LETTERS, 2002, 4 (22) :3947-3950
[3]   Catalysis by amino acid-derived tetracoordinate complexes: Enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes [J].
Dangel, BD ;
Polt, R .
ORGANIC LETTERS, 2000, 2 (19) :3003-3006
[4]   New soluble TADDOL-bearing polymers.: Preparation and their use as Ti-complex catalysts for enantio selective addition of diethylzinc to benzaldehyde [J].
Degni, S ;
Strandman, S ;
Laari, P ;
Nuopponen, M ;
Wilén, CE ;
Tenhu, H ;
Rosling, A .
REACTIVE & FUNCTIONAL POLYMERS, 2005, 62 (03) :231-240
[5]   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
[6]   Asymmetric C-C bond formation with L-prolinol derived chiral catalysts immobilized on polymer fibers [J].
Degni, S ;
Wilén, CE ;
Leino, R .
TETRAHEDRON-ASYMMETRY, 2004, 15 (02) :231-237
[7]   Heterogeneous asymmetric addition of diethylzinc to aromatic aldehydes catalyzed by Ti(IV)/imine bridged poly(R)-binaphthol [J].
Dong, C ;
Zhang, JL ;
Zheng, WH ;
Zhang, LF ;
Yu, ZL ;
Choi, MCK ;
Chan, ASC .
TETRAHEDRON-ASYMMETRY, 2000, 11 (12) :2449-2454
[8]   Synthesis and preliminary studies on a novel class of soluble amino alcohol reagents based on methacrylate copolymers [J].
Edwards, CW ;
Haddleton, DM ;
Morsley, D ;
Shipton, MR ;
Wills, M .
TETRAHEDRON, 2003, 59 (31) :5823-5830
[9]   ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY POLYMER-SUPPORTED CHIRAL OXAZABOROLIDINE [J].
ELMOUALIJ, N ;
CAZE, C .
EUROPEAN POLYMER JOURNAL, 1995, 31 (02) :193-198
[10]   New soluble bifunctional polymeric chiral ligands for enantioselectively catalytic reactions [J].
Fan, QH ;
Liu, GH ;
Deng, GJ ;
Chen, XM ;
Chan, ASC .
TETRAHEDRON LETTERS, 2001, 42 (51) :9047-9050