Indium tribromide:: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones

被引:83
作者
Bandini, M [1 ]
Cozzi, PG [1 ]
Melchiorre, P [1 ]
Umani-Ronchi, A [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
catalysis; cyanohydrins; indium; ketones;
D O I
10.1016/S0040-4039(01)00368-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic addition of trimethylsilyl cyanide (TMSCN) to a large variety of hetero-substituted ketones promoted by anhydrous InBr3 has been studied. The low catalytic loading (0.1-1 mol%) and the mild experimental conditions required represent the key features of this novel catalytic system. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3041 / 3043
页数:3
相关论文
共 22 条
[1]   First TiCl4-mediated diastereoselective reduction of α-nitro ketones to anti-β-nitro alcohols by BH3•SMe2 [J].
Ballini, R ;
Bosica, G ;
Marcantoni, E ;
Vita, P ;
Bartoli, G .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5854-5857
[2]   The asymmetric addition of trimethylsilyl cyanide to ketones catalysed by a bimetallic, chiral (salen)titanium complex [J].
Belokon, YN ;
Green, B ;
Ikonnikov, NS ;
North, M ;
Tararov, VI .
TETRAHEDRON LETTERS, 1999, 40 (46) :8147-8150
[3]  
Curini M, 1999, SYNLETT, P315
[4]   Structure/enantioselectivity study of the asymmetric addition of trimethylsilylcyanide to benzaldehyde catalyzed by Ti(IV)-Schiff base complexes [J].
Flores-Lopéz, LZ ;
Parra-Hake, M ;
Somanathan, R ;
Walsh, PJ .
ORGANOMETALLICS, 2000, 19 (11) :2153-2160
[5]   An efficient synthesis of dinitrile derivatives by the reaction of oxime esters or acid anhydrides with cyanotrimethylsilane catalyzed by La(O(i)Pr)3 [J].
Fujii, A ;
Sakaguchi, S ;
Ishii, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6209-6212
[6]  
GASSMAN PG, 1978, TETRAHEDRON LETT, V19, P3773
[7]   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
[8]   ADDITION OF TRIMETHYLSILYL CYANIDE TO ALPHA-SUBSTITUTED KETONES - CATALYST EFFICIENCY [J].
GREENLEE, WJ ;
HANGAUER, DG .
TETRAHEDRON LETTERS, 1983, 24 (42) :4559-4560
[9]   Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications [J].
Gregory, RJH .
CHEMICAL REVIEWS, 1999, 99 (12) :3649-3682
[10]  
GROUTAS WC, 1980, SYNTHESIS-STUTTGART, P861