Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance

被引:332
作者
Das, Shoubhik [1 ]
Addis, Daniele [1 ]
Zhou, Shaolin [1 ]
Junge, Kathrin [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
TERTIARY-AMINES; SELF-ENCAPSULATION; CARBONYL-COMPOUNDS; SILANE REDUCTION; HYDROSILYLATION; KETONES; POLYMETHYLHYDROSILOXANE; CARBOXAMIDES; EFFICIENT; HYDROSILATION;
D O I
10.1021/ja910083q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel zinc-catalyzed reduction of tertiary amides was developed. This system shows remarkable chemoselectivity and substrate scope tolerating ester, ether, nitro, cyano, azo, and keto substituents
引用
收藏
页码:1770 / +
页数:4
相关论文
共 44 条
[1]  
Anderson P. G, 2008, MODERN REDUCTION MET
[2]   Lewis acid catalyzed stereoselective hydrosilylation of ketones under the control of σ-π chelation [J].
Asao, N ;
Ohishi, T ;
Sato, K ;
Yamamoto, Y .
TETRAHEDRON, 2002, 58 (41) :8195-8203
[3]   Lewis acid-catalyzed trans-hydrosilylation of alkynes [J].
Asao, N ;
Sudo, T ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7654-7655
[4]   Highly chemoselective metal-free reduction of tertiary amides [J].
Barbe, Guillaume ;
Charette, Andr B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :18-+
[5]   [Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights [J].
Bette, V ;
Mortreux, A ;
Savoia, D ;
Carpentier, JF .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :289-302
[6]   New developments in zinc-catalyzed asymmetric hydrosilylation of ketones with PMHS [J].
Bette, V ;
Mortreux, A ;
Savoia, D ;
Carpentier, JF .
TETRAHEDRON, 2004, 60 (12) :2837-2842
[7]   New chiral 1,2-diamines and their use in zinc-catalyzed asymmetric hydrosilylation of acetophenone [J].
Bette, V ;
Mortreux, A ;
Ferioli, F ;
Martelli, G ;
Savoia, D ;
Carpentier, JF .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (14) :3040-3045
[8]   B(C6F5)3-catalyzed silation of alcohols:: A mild, general method for synthesis of silyl ethers [J].
Blackwell, JM ;
Foster, KL ;
Beck, VH ;
Piers, WE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4887-4892
[9]   STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-PARAHERQUAMIDE-B [J].
CUSHING, TD ;
SANZCERVERA, JF ;
WILLIAMS, RM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9323-9324
[10]   Reduction of amides with silanes catalyzed by MoO2Cl2 [J].
Fernandes, Ana C. ;
Romao, Carlos C. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 272 (1-2) :60-63