Polystyrene-anchored Cinchona ammonium salts:: Easily recoverable phase-transfer catalysts for the asymmetric synthesis of α-amino acids

被引:58
作者
Chinchilla, R
Mazón, P
Nájera, C
机构
[1] Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain
[2] Univ Alicante, ISO, E-03080 Alicante, Spain
关键词
alkylation; amino acids; ammonium salts; asymmetric synthesis; C-C bond formation; organic catalysis; phase-transfer catalysis;
D O I
10.1002/adsc.200404093
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Cinchonidine, epicinchonidine, cinchonine or quinine have been N-anchored to cross-linked polystyrene (Merrifield resin) or grafted polystyrene (Syn-Phase(TM) Lanterns) affording polymer-supported chiral ammonium salts which are employed as phase-transfer catalysts in the asymmetric alkylation of N-(diphenylmethylene)glycine esters. These new polymeric catalysts can be easily recovered after the reaction by simple filtration and reused.
引用
收藏
页码:1186 / 1194
页数:9
相关论文
共 111 条
[41]   Solid-phase organic reactions .2. A review of the literature Nov 95 Nov 96. [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, DC .
TETRAHEDRON, 1997, 53 (16) :5643-5678
[42]   MICHAEL REACTIONS CATALYZED BY POLYMER-SUPPORTED QUATERNARY AMMONIUM-SALTS DERIVED FROM CINCHONA AND EPHEDRA ALKALOIDS [J].
HODGE, P ;
KHOSHDEL, E ;
WATERHOUSE, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (09) :2205-2209
[43]   Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst [J].
Horikawa, M ;
Busch-Petersen, J ;
Corey, EJ .
TETRAHEDRON LETTERS, 1999, 40 (20) :3843-3846
[44]   Linkers for solid phase organic synthesis [J].
James, IW .
TETRAHEDRON, 1999, 55 (16) :4855-4946
[45]   Synthesis and application of dimeric Cinchona alkaloid phase-transfer catalysts:: α,α′-bis[O(9)-allylcinchonidinium]-o, m, or p-xylene dibromide [J].
Jew, SS ;
Jeong, BS ;
Yoo, MS ;
Huh, H ;
Park, HG .
CHEMICAL COMMUNICATIONS, 2001, (14) :1244-1245
[46]  
Kacprzak K, 2001, SYNTHESIS-STUTTGART, P961
[47]  
Kita T, 2002, ANGEW CHEM INT EDIT, V41, P2832, DOI 10.1002/1521-3773(20020802)41:15<2832::AID-ANIE2832>3.0.CO
[48]  
2-Q
[49]  
KOBAYASHI N, 1981, MAKROMOL CHEM-RAPID, V2, P105
[50]   Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation [J].
Ley, SV ;
Baxendale, IR ;
Bream, RN ;
Jackson, PS ;
Leach, AG ;
Longbottom, DA ;
Nesi, M ;
Scott, JS ;
Storer, RI ;
Taylor, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (23) :3815-4195