An efficient and facile one-pot synthesis of cyanohydrin esters from carbonyl compounds catalyzed by iron(III) chloride

被引:40
作者
Iwanami, K [1 ]
Aoyagi, M [1 ]
Oriyama, T [1 ]
机构
[1] Ibaraki Univ, Fac Sci, Mito, Ibaraki 3108512, Japan
关键词
cyanation; cyanohydrin ester; trimethylsilyl cyanide; acid anhydride; carbonyl compound; iron(III) chloride;
D O I
10.1016/j.tetlet.2005.09.003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of cyanohydrin esters were readily prepared from carbonyl compounds with trimethylsilyl cyanide and acid anhydride under the influence of a catalytic amount of iron(III) chloride in a convenient one-pot procedure. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7487 / 7490
页数:4
相关论文
共 39 条
[1]   Asymmetric catalysis of carbon-carbon bond-forming reactions using metal(salen) complexes [J].
Achard, TRJ ;
Clutterbuck, LA ;
North, M .
SYNLETT, 2005, (12) :1828-1847
[2]   Trimethylsilyl cyanide addition to carbonyl compounds under neutral condition catalyzed by iodine [J].
Azizi, N ;
Saidi, MR .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (10) :2111-2115
[3]   Indium tribromide:: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones [J].
Bandini, M ;
Cozzi, PG ;
Melchiorre, P ;
Umani-Ronchi, A .
TETRAHEDRON LETTERS, 2001, 42 (16) :3041-3043
[4]   Catalytic asymmetric synthesis of O-acetyl cyanohydrins from KCN, Ac2O and aldehydes [J].
Belokon, YN ;
Gutnov, AV ;
Moskalenko, MA ;
Yashkina, LV ;
Lesovoy, DE ;
Ikonnikov, NS ;
Larichev, VS ;
North, M .
CHEMICAL COMMUNICATIONS, 2002, (03) :244-245
[5]   Chemically catalyzed asymmetric cyanohydrin syntheses [J].
Brunel, JM ;
Holmes, IP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (21) :2752-2778
[6]   Synthesis of racemic tertiary cyanohydrins [J].
Chen, FX ;
Feng, XM .
SYNLETT, 2005, (06) :892-899
[7]   CYANOSILYLATION OF ALDEHYDES AND KETONES - CONVENIENT ROUTE TO CYANOHYDRIN DERIVATIVES [J].
EVANS, DA ;
TRUESDALE, LK ;
CARROLL, GL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (02) :55-56
[8]  
EVANS DA, 1973, TETRAHEDRON LETT, V14, P4929
[9]   ADDITION OF TERT-BUTYLDIMETHYLSILYL OR TERT-BUTYLDIPHENYLSILYL CYANIDE TO HINDERED KETONES [J].
GOLINSKI, M ;
BROCK, CP ;
WATT, DS .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :159-164
[10]   Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications [J].
Gregory, RJH .
CHEMICAL REVIEWS, 1999, 99 (12) :3649-3682