Tishchenko reactions and Oppenauer oxidation reactions of aldehydes promoted by diisobutylaluminum hydride

被引:24
作者
Hon, YS [1 ]
Chang, CP
Wong, YC
机构
[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan
[2] Acad Sinica, Inst Chem, Taipei 115, Taiwan
关键词
Tishchenko reaction; Oppenauer oxidation; alpha-silyloxyaldehyde; alpha-silyloxyketone;
D O I
10.1016/j.tetlet.2004.02.145
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aliphatic aldehydes react with catalytic amount of Dibal-H in n-pentane to give the corresponding Tishchenko products in good to excellent yields. Contrary, alpha-silyloxyaldehydes give alpha-silyloxyketones via Oppenauer oxidation under similar condition. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3313 / 3315
页数:3
相关论文
共 45 条
[1]  
Baidossi W, 1996, SYNTHESIS-STUTTGART, P1127
[2]   REACTIONS OF NORBORNYL ALDEHYDES WITH DIIRON NONACARBONYL - A STEREOSELECTIVE PATHWAY TO GEMINAL-FACED ESTERS AND ALCOHOLS [J].
BANKSTON, D .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :2003-2006
[3]  
Berberich H, 1998, ANGEW CHEM INT EDIT, V37, P1569, DOI 10.1002/(SICI)1521-3773(19980619)37:11<1569::AID-ANIE1569>3.0.CO
[4]  
2-C
[5]   HOMOGENEOUS CATALYSIS - CATALYTIC INTRAMOLECULAR CONVERSION OF 1,4-DIALDEHYDES TO GAMMA-LACTONES [J].
BERGENS, SH ;
FAIRLIE, DP ;
BOSNICH, B .
ORGANOMETALLICS, 1990, 9 (03) :566-571
[6]   EVIDENCE FOR C-O BOND FORMATION, ALDEHYDE DECARBONYLATION, AND DIMERIZATION BY REACTION OF FORMALDEHYDE AND ACETALDEHYDE WITH TRANS-ROIR(CO)(PPH3)2 [J].
BERNARD, KA ;
ATWOOD, JD .
ORGANOMETALLICS, 1988, 7 (01) :235-236
[7]  
BUNCE RA, 1987, J ORG PREP P INT, V19, P161
[8]   SYNTHESIS AND REACTIONS OF NICKEL AND PALLADIUM CARBON-BOUND ENOLATE COMPLEXES [J].
BURKHARDT, ER ;
BERGMAN, RG ;
HEATHCOCK, CH .
ORGANOMETALLICS, 1990, 9 (01) :30-44
[9]  
CHANG CP, 2002, CHEMISTRY TAIPEI, V60, P561
[10]   NEW SEQUENTIAL CARBON-CARBON BOND FORMING REACTIONS - A SAMARIUM(II) IODIDE MEDIATED VINYLOGOUS BARBIER REACTION FOLLOWED BY AN ALDOL REACTION [J].
CURRAN, DP ;
WOLIN, RL .
SYNLETT, 1991, (05) :317-318