Conjugate reduction of α,β-unsaturated carbonyl compounds.: Selective inhibition of benzyl ether hydrogenolysis by NH4OH/MeOH

被引:6
作者
Dias, LC [1 ]
Campano, PL [1 ]
机构
[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil
关键词
conjugate reduction; inhibition of benzyl ether hydrogenolysis; chemoselective reduction of alpha; beta-unsaturated compounds; selective catalytic hydrogenation;
D O I
10.1590/S0103-50531998000100017
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of alpha,beta-unsaturated alkyl and aryl ketones, esters and N-methoxy-N-methyl-amides (Weinreb amides) containing an O-benzyl protecting group undergo conjugate reduction by H-2/Pd/C in the presence of 2N NH4OH/MeOH at room temperature and ordinary pressure leaving the benzyl group intact.
引用
收藏
页码:97 / 99
页数:3
相关论文
共 15 条
[1]   EFFECT OF AMINES ON O-BENZYL GROUP HYDROGENOLYSIS [J].
CZECH, BP ;
BARTSCH, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :4076-4078
[2]   CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY CATECHOLBORANE [J].
EVANS, DA ;
FU, GC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5678-5680
[3]   ENANTIOSPECIFIC SYNTHESES OF DEOXYMANNOJIRIMYCIN, FAGOMINE AND 2R,5R-DIHYDROXYMETHYL-3R,4R-DIHYDROXYPYRROLIDINE FROM D-GLUCOSE [J].
FLEET, GWJ ;
SMITH, PW .
TETRAHEDRON LETTERS, 1985, 26 (11) :1469-1472
[4]   Reaction of a 1-azirine-3-methylacrylate and derivatives with diphenylketene. A convenient route to 5-pyrrolin-2-ones. [J].
Kascheres, A ;
Nunes, J ;
Brandao, F .
TETRAHEDRON, 1997, 53 (21) :7089-7096
[5]   HIGHLY CHEMOSELECTIVE PALLADIUM-CATALYZED CONJUGATE REDUCTION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH SILICON HYDRIDES AND ZINC-CHLORIDE COCATALYST [J].
KEINAN, E ;
GREENSPOON, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7314-7325
[6]  
KOENIG TM, 1990, TETRAHEDRON LETT, V31, P323
[7]  
Larock R. C, 1989, COMPREHENSIVE ORGANI, P8
[8]  
MAHONEY WS, 1988, J AM CHEM SOC, V110, P29
[9]   CHEMISTRY OF 4-MEMBERED CYCLIC NITRONES .5. SYNTHESIS AND OXIDATION OF 1-HYDROXYAZETIDINES [J].
PENNINGS, MLM ;
REINHOUDT, DN .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4043-4048
[10]  
Rylander P., 1985, HYDROGENATION METHOD, P148