REDUCTIONS OF CARBOXYLIC-ACIDS AND THEIR DERIVATIVES USING SAMARIUM DIIODIDE-ACID SYSTEM

被引：32

作者：

KAMOCHI, Y

KUDO, T

机构：

[1] Daiichi College of Pharmaceutical Sciences, Minami-ku, Fukuoka, 815

来源：

TETRAHEDRON | 1992年 / 48卷 / 21期

关键词：

SAMARIUM DIIODIDE-ACID SYSTEM; AROMATIC ALDEHYDE SYNTHESIS;

D O I：

10.1016/S0040-4020(01)80441-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carboxylic acid was converted to alcohol in a facile-rapid reduction using samarium diiodide in protic solvent under a basic or acidic medium at room temperature in high yield. A similar reaction of ester and anhydride reduced to the corresponding alcohol as the major products and nitrile afforded amine. Amide was rapidly reduced under a basic medium to afford alcohol, but the reduction with samarium diiodide-acid system of amide gave aldehyde in quantitative yield.

引用

页码：4301 / 4312

页数：12

共 33 条

[1] LITHIUM DIETHOXYALUMINOHYDRIDE AS A SELECTIVE REDUCING AGENT - THE REDUCTION OF DIMETHYLAMIDES TO ALDEHYDES
BROWN, HC
TSUKAMOTO, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (02) : 502 - 503
[2] SELECTIVE REDUCTIONS .1. PARTIAL REDUCTION OF TERTIARY AMIDES WITH LITHIUM ALUMINUM HYDRIDE - A NEW ALDEHYDE SYNTHESIS VIA 1-ACYLAZIRIDINES
BROWN, HC
TSUKAMOTO, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (22) : 4549 - &
[3] REDUCTIVE COUPLINGS OF ACID-CHLORIDES MEDIATED BY SMI2
COLLIN, J
DALLEMER, F
NAMY, JL
KAGAN, HB
[J]. TETRAHEDRON LETTERS, 1989, 30 (52) : 7407 - 7410
[4] Cope A. C., 1963, ORG SYNTH, VIV, P339
[5] THE PHOTODIMERISATION OF SOME UNSATURATED CYCLIC SULPHONES
DAVIES, W
JAMES, FC
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1955, : 314 - 317
[6] SAMARIUM-CATALYZED INTRAMOLECULAR TISHCHENKO REDUCTION OF BETA-HYDROXY KETONES - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF DIFFERENTIATED ANTI 1,3-DIOL MONOESTERS
EVANS, DA
HOVEYDA, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6447 - 6449
[7] REACTIVITY OF (C5ME5)2SM WITH ARYL-SUBSTITUTED ALKENES - SYNTHESIS AND STRUCTURE OF A BIMETALLIC STYRENE COMPLEX THAT CONTAINS AN ETA-2-ARENE LANTHANIDE INTERACTION
EVANS, WJ
ULIBARRI, TA
ZILLER, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) : 219 - 223
[8] REACTIVITY OF (C5ME5)2SM AND RELATED SPECIES WITH ALKENES - SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF A SERIES OF ORGANOSAMARIUM ALLYL COMPLEXES
EVANS, WJ
ULIBARRI, TA
ZILLER, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) : 2314 - 2324
[9] A SAMARIUM(II) IODIDE PROMOTED TANDEM RADICAL CYCLIZATION - THE TOTAL SYNTHESIS OF (+/-)-HYPNOPHILIN AND THE FORMAL SYNTHESIS OF (+/-)-CORIOLIN
FEVIG, TL
ELLIOTT, RL
CURRAN, DP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) : 5064 - 5067
[10] SAMARIUM(II) DI-IODIDE INDUCED REDUCTIVE COUPLING OF ALPHA,BETA-UNSATURATED ESTERS WITH CARBONYL-COMPOUNDS LEADING TO A FACILE SYNTHESIS OF GAMMA-LACTONE
FUKUZAWA, S
NAKANISHI, A
FUJINAMI, T
SAKAI, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1669 - 1675

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