Selective reduction of carbonyl groups in the presence of low-valent titanium reagents

被引:18
作者
Lin, Wei [1 ]
Hu, Ming-Hua [1 ]
Feng, Xian [1 ]
Fu, Lei [1 ]
Cao, Cheng-Pao [1 ]
Huang, Zhi-Bin [1 ]
Shi, Da-Qing [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
关键词
Chemoselective reduction; Carbonyl groups; Low-valent titanium reagent; HIGHLY REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; CHEMOSELECTIVE REDUCTION; TRANSFER HYDROGENATION; UNSATURATED-KETONES; AID; DERIVATIVES; COMPLEXES; ALDEHYDES; HYDROSILYLATION;
D O I
10.1016/j.tetlet.2014.02.072
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2238 / 2242
页数:5
相关论文
共 54 条
[1]   Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Amino Acid Derived Rhodium Complexes: On the Origin of Enantioselectivity and Enantioswitchability [J].
Ahlford, Katrin ;
Ekstrom, Jesper ;
Zaitsev, Alexey B. ;
Ryberg, Per ;
Eriksson, Lars ;
Adolfsson, Hans .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (42) :11197-11209
[2]   The biphasic transfer hydrogenation of aldehydes and ketones with isopropanol catalyzed by water-soluble rhodium complexes [J].
Ajjou, AN ;
Pinet, JL .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 214 (02) :203-206
[3]  
[Anonymous], ANGEW CHEM
[4]   Selective C=O Reduction in Phthalimide with Nickel(0) Compounds [J].
Arevalo, Alma ;
Ovando-Segovia, Sebastian ;
Flores-Alamo, Marcos ;
Garcia, Juventino J. .
ORGANOMETALLICS, 2013, 32 (10) :2939-2943
[5]  
Bannem L. C., 2004, W0200405068A2, Patent No. 200405068
[6]  
Blasko G., 1997, [No title captured], Patent No. [9736895, WO 9736895]
[7]   Efficient and Selective Hydrosilylation of Carbonyl Compounds Catalyzed by Iron Acetate and N-Hydroxyethylimidazolium Salts [J].
Buitrago, Elina ;
Tinnis, Fredrik ;
Adolfsson, Hans .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (01) :217-222
[8]   Sodium borohydride reduction of ketones, aldehydes and imines using PEG400 as catalyst without solvent [J].
Cao, YQ ;
Dai, Z ;
Chen, BH ;
Liu, R .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2005, 80 (07) :834-836
[9]   Hydroacylation of activated ketones catalyzed by N-heterocyclic carbenes [J].
Chan, A ;
Scheidt, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) :4558-4559
[10]   Solvent-free reduction of aldehydes and ketones using solid acid-activated sodium borohydride [J].
Cho, Byung Tae ;
Kang, Sang Kyu ;
Kim, Min Sung ;
Ryu, Soo Ryeon ;
An, Duk Keun .
TETRAHEDRON, 2006, 62 (34) :8164-8168