[HC(PY)3W(NO)2(CO)](SBF6)2 AS A LEWIS ACID PRECURSOR IN ADDITIONS OF SILYLATED C-NUCLEOPHILES TO CARBONYL-COMPOUNDS

被引:29
作者
FALLER, JW
GUNDERSEN, LL
机构
[1] Yale University, Department of Chemistry, New Haven, CT 06511-8118
关键词
D O I
10.1016/S0040-4039(00)77592-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[HC(PY)3W(NO)2(CO)](SbF6)2 is a feasible Lewis acid catalyst precursor for the addition of silylated C-nucleophiles to carbonyl compounds. The O-silylated adducts are easily isolated without aqueous wort-up and the catalyst can be recycled. A remarkable solvent effect is found in the addition of TMS-CN to cyclohexanones.
引用
收藏
页码:2275 / 2278
页数:4
相关论文
共 13 条
[1]   STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUND ADDITION TO KETONES [J].
ASHBY, EC ;
LAEMMLE, JT .
CHEMICAL REVIEWS, 1975, 75 (04) :521-546
[2]   CATIONIC MONONUCLEAR AND BINUCLEAR IRON COMPLEXES AS LEWIS ACID CATALYSTS IN MUKAIYAMA REACTIONS [J].
BACH, T ;
FOX, DNA ;
REETZ, MT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) :1634-1636
[3]  
COLWIN EW, 1985, SILICON ORGANIC SYNT
[4]   SYNTHETIC APPLICATIONS OF TRIMETHYLSILYL CYANIDE - EFFICIENT SYNTHESIS OF BETA-AMINOMETHYL ALCOHOLS [J].
EVANS, DA ;
CARROLL, GL ;
TRUESDALE, LK .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) :914-917
[5]   STRONG LEWIS-ACIDS DERIVED FROM MOLYBDENUM AND TUNGSTEN NITROSYLS CONTAINING THE TRI-2-PYRIDYLMETHANE LIGAND - DYNAMIC NMR-STUDIES OF THEIR ADDUCTS WITH ALDEHYDES, KETONES, AND ESTERS [J].
FALLER, JW ;
MA, YN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1579-1586
[6]   ORGANOLANTHANIDE CATALYSIS OF A MUKAIYAMA ADDITION-REACTION [J].
GONG, L ;
STREITWIESER, A .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6235-6236
[7]  
GROUTAS WC, 1980, SYNTHESIS-STUTTGART, P861
[8]   LANTHANIDE TRIFLUOROMETHANESULFONATES AS REUSABLE CATALYSTS - MICHAEL AND DIELS-ALDER REACTIONS [J].
KOBAYASHI, S ;
HACHIYA, I ;
TAKAHORI, T ;
ARAKI, M ;
ISHITANI, H .
TETRAHEDRON LETTERS, 1992, 33 (45) :6815-6818
[9]   YTTERBIUM TRICYANIDE, A HIGHLY EFFICIENT CATALYST FOR THE ADDITION OF CYANOTRIMETHYLSILANE TO CARBONYL-COMPOUNDS [J].
MATSUBARA, S ;
TAKAI, T ;
UTIMOTO, K .
CHEMISTRY LETTERS, 1991, (08) :1447-1450
[10]   AN UNEXPECTED ACYLOIN REARRANGEMENT AND OXIDATION OF A CAMPHOR DERIVATIVE [J].
MCINTOSH, JM ;
CASSIDY, KC .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (08) :1315-1319