Designer Lewis acid catalysts - bulky aluminium reagents for selective organic synthesis

被引:111
作者
Saito, S [1 ]
Yamamoto, H [1 ]
机构
[1] NAGOYA UNIV, GRAD SCH ENGN, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN
关键词
D O I
10.1039/a607464b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sterically hindered aluminium aryloxides have been developed as designer Lewis acid catalysts for stereo-, regio- and chemo-selective carbon-carbon bond-forming reactions. Compared with classical Lewis acids, these aluminium reagents coordinate strongly with various oxygen-containing substrates, and this coordination is affected by the steric environment of their ligands, The carbonyl groups of the bound substrates are either electronically activated or sterically deactivated depending on the aluminium reagent used and the type of reaction, Designer chiral catalysts based on the structure of these bulky aluminium reagents have also been examined.
引用
收藏
页码:1585 / 1592
页数:8
相关论文
共 39 条
[1]   THE LEWIS ACID COMPLEXES OF ALPHA,BETA-UNSATURATED CARBONYL AND NITRILE COMPOUNDS .1. A NUCLEAR MAGNETIC-RESONANCE STUDY [J].
CHILDS, RF ;
MULHOLLAND, DL ;
NIXON, A .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (06) :801-808
[2]  
Elschenbroich C., 1992, ORGANOMETALLICS
[3]   SYNTHESIS AND STRUCTURE OF AL(OAR-ASTERISK)3 (AR-ASTERISK=2,6-TBU2-4-MEC6H2) - THE 1ST 3-COORDINATE HOMOLEPTIC ALUMINUM ARYLOXIDE [J].
HEALY, MD ;
BARRON, AR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (07) :921-922
[4]   MOLECULAR DESIGN OF A CHIRAL LEWIS-ACID FOR THE ASYMMETRIC CLAISEN REARRANGEMENT [J].
MARUOKA, K ;
SAITO, S ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :1165-1166
[5]   STABILIZATION OF REACTIVE ALDEHYDES BY COMPLEXATION WITH METHYLALUMINUM BIS(2,6-DIPHENYLPHENOXIDE) AND THEIR SYNTHETIC APPLICATION [J].
MARUOKA, K ;
CONCEPCION, AB ;
MURASE, N ;
OISHI, M ;
HIRAYAMA, N ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3943-3949
[6]  
MARUOKA K, 1995, SYNLETT, P719
[7]   METHYLALUMINUM BIS(2,6-DI-TERT-BUTYL-4-METHYLPHENOXIDE) AS A PROTECTING GROUP FOR MULTIFUNCTIONAL MOLECULES - SYNTHETIC UTILITY IN SELECTIVE CARBONYL REDUCTIONS [J].
MARUOKA, K ;
ARAKI, Y ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2650-2652
[8]   ASYMMETRIC DIELS-ALDER REACTION OF CYCLOPENTADIENE AND METHYL ACRYLATE CATALYZED BY CHIRAL ORGANOALUMINUM REAGENTS [J].
MARUOKA, K ;
CONCEPCION, AB ;
YAMAMOTO, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (12) :3501-3503
[9]   UNPRECEDENTED STEREOCHEMICAL CONTROL IN THE ORGANOALUMINUM-PROMOTED INTRAMOLECULAR ENE REACTIONS OF DELTA,EPSILON-UNSATURATED ALDEHYDES [J].
MARUOKA, K ;
OOI, T ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) :9011-9012
[10]  
MARUOKA K, 1993, SYNLETT, P197