Diastereoselective reduction of acyclic hydroxyketones and diketones with an indium hydride reagent

被引:31
作者
Yamada, M [1 ]
Horie, T [1 ]
Kawai, M [1 ]
Yamamura, H [1 ]
Araki, S [1 ]
机构
[1] NAGOYA INST TECHNOL,DEPT APPL CHEM,SHOWA KU,NAGOYA,AICHI 466,JAPAN
关键词
D O I
10.1016/S0040-4020(97)10024-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydroxyketones and diketones have been reduced with lithium indium hydride to give meso-diols selectively. alpha-Hydroxyketones and alpha-diketones are reduced to meso-1,2-diols with high diastereoselectivities, whereas the selectivities of beta-hydroxyketones and beta-diketones are less satisfactory. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:15685 / 15690
页数:6
相关论文
共 32 条
[1]   The acylation of methyl ketones with aliphatic esters by means of sodium amide synthesis of beta-diketones of the type RCOCH2COR [J].
Adams, JT ;
Hauser, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1220-1222
[2]   PHOTOCHEMICAL-REACTION OF ALCOHOLS .1. IRRADIATION OF ALIPHATIC-ALCOHOLS [J].
BALSELLS, RE ;
FRASCA, AR .
TETRAHEDRON, 1982, 38 (02) :245-255
[3]   BORON MEDIATED ONE-POT ALDOL-REDUCTION SEQUENCE - ENANTIO AND DIASTEREOSELECTIVE SYNTHESIS OF TYPICAL POLYKETIDE FRAGMENTS [J].
BONINI, C ;
RACIOPPI, R ;
RIGHI, G ;
ROSSI, L .
TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :173-176
[4]   ALUMINUM-HYDRIDE REDUCTION OF ALPHA-KETOLS .2. ADDITIONAL EVIDENCE FOR CONFORMATIONAL FLEXIBILITY IN TRANSITION-STATE [J].
BOWLUS, SB ;
KATZENEL.JA .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) :3309-3314
[5]   SELECTIVE REDUCTIONS .8. STEREOCHEMISTRY OF REDUCTION OF CYCLIC AND BICYCLIC KETONES BY ALKOXY-SUBSTITUTED LITHIUM ALUMINUM HYDRIDES [J].
BROWN, HC ;
DECK, HR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (24) :5620-&
[6]   ORGANIC-ANIONS .1. EQUILIBRATION OF 1,3-DIARYLPROPENES [J].
BUSHBY, RJ ;
FERBER, GJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (14) :1683-1688
[7]   REDUCTION OF SYMMETRICAL 1,2- AND 1,3-DIKETONES WITH SODIUM BOROHYDRIDE, AND SEPARATION OF DIASTEREOISOMERIC 1,2- AND 1,3-DIOLS BY MEANS OF BORATE COMPLEXES [J].
DALE, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (MAR) :910-&
[8]   REDUCTION OF SOME ENOLIZABLE-BETA-DICARBONYL COMPOUNDS TO UNSATURATED ALCOHOLS BY LITHIUM ALUMINUM HYDRIDE .2. BETA-DIKETONES [J].
DREIDING, AS ;
HARTMAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3723-3726
[9]  
EASTWOOD FW, 1970, TETRAHEDRON LETT, P5223
[10]   SAMARIUM-CATALYZED INTRAMOLECULAR TISHCHENKO REDUCTION OF BETA-HYDROXY KETONES - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF DIFFERENTIATED ANTI 1,3-DIOL MONOESTERS [J].
EVANS, DA ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6447-6449