Lithium chloride: An active and simple catalyst for cyanosilylation of aldehydes and ketones

被引:135
作者
Kurono, N [1 ]
Yamaguchi, M [1 ]
Suzuki, K [1 ]
Ohkuma, T [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan
关键词
D O I
10.1021/jo050791t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
LiCl acts as a highly effective catalyst for cyanosilylation of various aldehydes and ketones to the corresponding silylated cyanohydrins. The reaction proceeds smoothly with a substrate/catalyst molar ratio of 100-100 000 at 20-25 degrees C under solvent-free conditions. alpha,beta-Unsaturated aldehydes are completely converted to the 1,2-adducts. The cyanation products can be isolated by direct distillation of the reaction mixture.
引用
收藏
页码:6530 / 6532
页数:3
相关论文
共 62 条
[1]   A BMPD-yttrium isopropoxide complex: Highly efficient chiral Lewis acid catalyst for asymmetric silylcyanation [J].
Abiko, A ;
Wang, GQ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2264-2265
[2]   An improved synthesis of cyanohydrins in the presence of solid LiClO4 under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 688 (1-2) :283-285
[3]   Vanadyl salen complexes covalently anchored to an imidazolium ion as catalysts for the cyanosilylation of aldehydes in ionic liquids [J].
Baleizao, C ;
Gigante, B ;
Garcia, H ;
Corma, A .
TETRAHEDRON LETTERS, 2003, 44 (36) :6813-6816
[4]  
Bandini M, 2002, EUR J ORG CHEM, V2002, P3243
[5]   Vanadium-catalyzed asymmetric cyanohydrin synthesis [J].
Belokon, YN ;
North, M ;
Parsons, T .
ORGANIC LETTERS, 2000, 2 (11) :1617-1619
[6]   The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes [J].
Belokon, YN ;
Caveda-Cepas, S ;
Green, B ;
Ikonnikov, NS ;
Krustalev, VN ;
Larichev, VS ;
Moscalenko, MA ;
North, M ;
Orizu, C ;
Tararov, VI ;
Tasinazzo, M ;
Timofeeva, GI ;
Yashkina, LV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :3968-3973
[7]   ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF ALDEHYDES [J].
BOLM, C ;
MULLER, P .
TETRAHEDRON LETTERS, 1995, 36 (10) :1625-1628
[8]   Methyltriphenylphosphonium iodide catalyzes the addition of trimethylsilyl cyanide to aldehydes [J].
Córdoba, R ;
Plumet, J .
TETRAHEDRON LETTERS, 2003, 44 (32) :6157-6159
[9]   ENANTIOSELECTIVE CONVERSION OF ALDEHYDES TO CYANOHYDRINS BY A CATALYTIC-SYSTEM WITH SEPARATE CHIRAL BINDING-SITES FOR ALDEHYDE AND CYANIDE COMPONENTS [J].
COREY, EJ ;
WANG, Z .
TETRAHEDRON LETTERS, 1993, 34 (25) :4001-4004
[10]   BIS(HYDROXYPHENYLOXAZOLINATO)-TITANIUM(IV) AND BIS(HYDROXYPHENYLOXAZOLINATO)-ZIRCONIUM(IV) TRIFLATES AS A NOVEL TRANSITION METAL-BASED LEWIS-ACIDS [J].
COZZI, PG ;
FLORIANI, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (20) :2557-2563