Chiral Lewis acid catalysts in Diels-Alder cycloadditions: Mechanistic aspects and synthetic applications of recent systems

被引:189
作者
Dias, LC [1 ]
机构
[1] UNIV ESTADUAL CAMPINAS, UNICAMP, INST QUIM, BR-13083970 CAMPINAS, SP, BRAZIL
关键词
asymmetric Diels-Alder cycloaddition reaction; chiral Lewis acids; asymmetric catalysis; dienophile-Lewis acid complex;
D O I
10.1590/S0103-50531997000400002
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review summarizes the recent progress which has been made in the use of chiral Lewis Acid catalysts in Diels-Alder cycloaddition reactions. Chiral catalysts containing aluminum, boron, titanium, copper, lanthanides, magnesium and transition-metals are critically reviewed. Structural studies on Lewis acid carbonyl complexes and synthetic applications of recent systems are specifically discussed.
引用
收藏
页码:289 / 332
页数:44
相关论文
共 214 条
[1]   COMPLEXES CONTAINING A LEWIS-ACID AND BRONSTED ACID FOR THE CATALYTIC ASYMMETRIC DIELS-ALDER REACTION [J].
AGGARWAL, VK ;
ANDERSON, E ;
GILES, R ;
ZAPARUCHA, A .
TETRAHEDRON-ASYMMETRY, 1995, 6 (06) :1301-1306
[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]   Defining the conformation of Lewis acid Lewis base complexes: Crystallographic evidence for simultaneous sigma and pi donation by a carbonyl group to a divalent boron Lewis acid [J].
Amendola, MC ;
Stockman, KE ;
Hoic, DA ;
Davis, WM ;
Fu, GC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :267-269
[4]  
[Anonymous], CATALYTIC ASYMMETRIC
[5]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[6]  
[Anonymous], COMPREHENSIVE ORGANI
[7]  
[Anonymous], ASYMMETRIC SYNTHESIS
[8]  
[Anonymous], ANGEW CHEM INT EDIT
[9]   Investigation of dienophile-TiCL(4) complexation by means of X-ray absorption and C-13-NMR spectroscopies [J].
Assfeld, X ;
Garcia, J ;
Garcia, JI ;
Mayoral, JA ;
Proietti, MG ;
RuizLopez, MF ;
Sanchez, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05) :1636-1642
[10]   VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS [J].
BAO, JM ;
WULFF, WD ;
RHEINGOLD, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3814-3815