Recent development and application of chiral phase-transfer catalysts

被引:690
作者
Hashimoto, Takuya [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/cr068368n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A review on the asymmetric reactions with various types of chiral quaternary ammonium salts which is used as the phase-transfer catalysts is presented which shows off the variations of the molecular designs and synthetic applications. The topics discussed include the alkylation, the Michael addition, the aldol reaction, Mannich reaction, Darzens reaction, the Neber rearrangement, epoxidation, aziridination, dihydroxylation, fluorination, and the Strecker reaction. Chiral phase-transfer catalysts maybe developed with the reliance on the molecular design of both the natural product-derived and purely synthetic chiral quaternary ammonium salts. This development provides new synthetic opportunities by expanding the applicability of this catalysis in modern organic synthesis.
引用
收藏
页码:5656 / 5682
页数:27
相关论文
共 199 条
[31]   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
[32]   Improved conditions for the asymmetric synthesis of α-amino acids using Cinchona-derived anthracenylmethyl ammonium salts as chiral phase-transfer organocatalysts [J].
Chinchilla, Rafael ;
Najera, Carmen ;
Ortega, Francisco J. .
TETRAHEDRON-ASYMMETRY, 2006, 17 (24) :3423-3429
[33]   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
[34]   Immobilization of catalysts derived from Cinchona alkaloids on modified poly(ethylene glycol) [J].
Danelli, T ;
Annunziata, R ;
Benaglia, M ;
Cinquini, M ;
Cozzi, F ;
Tocco, G .
TETRAHEDRON-ASYMMETRY, 2003, 14 (04) :461-467
[35]  
Dehmlow E. V., 1993, Phase Transfer Catalysis
[36]  
Dehmlow EV, 2002, EUR J ORG CHEM, V2002, P2087
[37]   Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction [J].
Dere, RT ;
Pal, RR ;
Patil, PS ;
Salunkhe, MM .
TETRAHEDRON LETTERS, 2003, 44 (28) :5351-5353
[38]   EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS [J].
DOLLING, UH ;
DAVIS, P ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :446-447
[39]   Formation of scalemic α,β-epoxysulfones [J].
Dorow, RL ;
Tymonko, SA .
TETRAHEDRON LETTERS, 2006, 47 (15) :2493-2495
[40]   Contrast performance in catalytic ability -: new cinchona phase transfer catalysts for asymmetric synthesis of α-amino acids [J].
Elango, S ;
Venugopal, M ;
Suresh, PS ;
Eni .
TETRAHEDRON, 2005, 61 (06) :1443-1447