CHEMOSELECTIVE CARBONYL REDUCTION MEDIATED BY LOW-VALENT TITANIUM

被引:5
作者
ADAMS, CM
SCHEMENAUR, JE
机构
[1] Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma
基金
美国国家科学基金会;
关键词
D O I
10.1080/00397919008053181
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Utilizing the rate difference in alkoxy alkyl radical formation from aldehydes versus ketones with low-valent titanium, aldehydes are preferentially reduced with tributyltin hydride. The difference in reactivity allows aldehydes to be reduced in the presence of ketones without laborious protection-deprotection steps. © 1990, Taylor & Francis Group, LLC. All rights reserved.
引用
收藏
页码:2359 / 2364
页数:6
相关论文
共 16 条
[1]   REDUCTION OF KETONES BY TRIBUTYLTIN HYDRIDE - THE EFFECT OF HIGH-PRESSURE ON STERIC HINDRANCE AND REARRANGEMENT PROCESSES [J].
DEGUEILCASTAING, M ;
RAHM, A ;
DAHAN, N .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1672-1676
[2]   REDUCTION BY TRIBUTYLTIN HYDRIDE OF CARBONYL-COMPOUNDS ADSORBED ON SILICA-GEL - SELECTIVE REDUCTION OF ALDEHYDES [J].
FUNG, NYM ;
MAYO, PD ;
SCHAUBLE, JH ;
WEEDON, AC .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3977-3979
[3]  
GIESE B, 1986, ORGANIC CHEM SERIES, V5
[4]  
Kuivila H. G., 1970, SYNTHESIS-STUTTGART, P499
[5]   REDUCTION OF SOME ALDEHYDES AND KETONES WITH ORGANOTIN HYDRIDES [J].
KUIVILA, HG ;
BEUMEL, OF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (05) :1246-&
[6]  
LAROCK RC, 1989, COMPREHENSIVE ORGANI, P535
[7]   CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM [J].
MCMURRY, JE .
CHEMICAL REVIEWS, 1989, 89 (07) :1513-1524
[8]   TITANIUM-INDUCED DICARBONYL-COUPLING REACTIONS [J].
MCMURRY, JE .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (11) :405-411
[9]  
NEWMAN WP, 1963, ANGEW CHEM INT EDIT, V2, P100
[10]   FREE-RADICAL MACROCYCLIZATION-TRANSANNULAR CYCLIZATION [J].
PORTER, NA ;
CHANG, VHT ;
MAGNIN, DR ;
WRIGHT, BT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3554-3560