New polymer-supported chiral phase-transfer catalysts in the asymmetric synthesis of α-amino acids:: the role of a spacer

被引:65
作者
Thierry, B [1 ]
Plaquevent, JC [1 ]
Cahard, D [1 ]
机构
[1] Univ Rouen, IRCOF, UPRESA 6014, F-76821 Mt St Aignan, France
关键词
D O I
10.1016/S0957-4166(01)00187-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Polymer-supported cinchona alkaloid salts with different spacers were used as phase-transfer catalysts in the asymmetric C-alkylation of N-diphenyl methylene glycine tert-butyl ester. Various catalysts and alkylation conditions were studied, the best result being 81% e.e. with cinchoninium iodide bound to polqstyrene with a four-carbon spacer. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:983 / 986
页数:4
相关论文
共 16 条
[1]   Asymmetric synthesis of α-amino acids using polymer-supported Cinchona alkaloid-derived ammonium salts as chiral phase-transfer catalysts [J].
Chinchilla, R ;
Mazón, P ;
Nájera, C .
TETRAHEDRON-ASYMMETRY, 2000, 11 (16) :3277-3281
[2]   ASYMMETRIC INDUCTION IN DARZENS REACTION BY MEANS OF CHIRAL PHASE-TRANSFER IN A 2-PHASE SYSTEM - EFFECT OF BINDING CATALYST TO A SOLID POLYMERIC SUPPORT [J].
COLONNA, S ;
FORNASIER, R ;
PFEIFFER, U .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (01) :8-11
[3]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[4]  
DESOUZA JA, 1996, TETRAHEDRON LETT, V37, P3183
[5]   RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
DUTHALER, RO .
TETRAHEDRON, 1994, 50 (06) :1539-1650
[6]   BROMINATION AND LITHIATION - 2 IMPORTANT STEPS IN FUNCTIONALIZATION OF POLYSTYRENE RESINS [J].
FARRALL, MJ ;
FRECHET, JMJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (24) :3877-3882
[7]   SOME NOVEL POLYMER-SUPPORTED OPTICALLY-ACTIVE PHASE-TRANSFER CATALYSTS .1. SYNTHESIS [J].
FRECHET, JMJ ;
KELLY, J ;
SHERRINGTON, DC .
POLYMER, 1984, 25 (10) :1491-1498
[8]  
KOBAYASHI N, 1981, MAKROMOL CHEM-RAPID, V2, P105
[9]   A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of alpha-amino acids [J].
Lygo, B ;
Wainwright, PG .
TETRAHEDRON LETTERS, 1997, 38 (49) :8595-8598
[10]   Enantioselective solid-phase synthesis of α-amino acid derivatives [J].
O'Donnell, MJ ;
Delgado, F ;
Pottorf, RS .
TETRAHEDRON, 1999, 55 (20) :6347-6362