FLUORIDE MEDIATED REACTIONS OF LACTONES WITH SILYL KETENE ACETALS

被引:15
作者
CSUK, R
SCHAADE, M
机构
[1] Pharmazeutisch-Chemisches Institut, Universität Heidelberg, D-69120 Heidelberg
关键词
ALDOLISATION REACTIONS; SILYL KETENE ACETALS; LACTONES; CARBOHYDRATES;
D O I
10.1016/S0040-4020(01)87014-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldolisation reactions of silyl ketene acetals with lactone carbonyls can be performed under very mild conditions in good yields in the presence of 5-10 mol-% of TMSF(2).
引用
收藏
页码:3333 / 3348
页数:16
相关论文
共 35 条
[1]  
ALIMAN LJ, 1971, TETRAHEDRON LETT, P4709
[2]   THE CHEMISTRY OF NITRATE ESTERS [J].
BOSCHAN, R ;
MERROW, RT ;
VANDOLAH, RW .
CHEMICAL REVIEWS, 1955, 55 (03) :485-510
[3]   REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].
CHUIT, C ;
CORRIU, RJP ;
REYE, C ;
YOUNG, JC .
CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448
[4]  
Cohen N., 1985, ORG SYNTH, V63, P127
[5]   CONVENIENT FLUORIDE-MEDIATED REACTIONS OF LACTONES WITH SILYL KETENE ACETALS [J].
CSUK, R ;
SCHAADE, M .
TETRAHEDRON LETTERS, 1993, 34 (49) :7907-7910
[6]   CHAIN ELONGATION OF ALDONOLACTONES [J].
CSUK, R ;
GLANZER, BI .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (06) :809-822
[7]   REACTIONS OF GLUCURONIC ACID .7. OXIDATIONS ON D-GLUCOFURANOSIDURONO-6,3-LACTONES [J].
DAX, K ;
WEIDMANN, H .
CARBOHYDRATE RESEARCH, 1972, 25 (02) :363-370
[8]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[9]   SYNTHESIS OF (TRIMETHYLSILYL)THIAZOLES AND REACTIONS WITH CARBONYL-COMPOUNDS - SELECTIVITY ASPECTS AND SYNTHETIC UTILITY [J].
DONDONI, A ;
FANTIN, G ;
FOGAGNOLO, M ;
MEDICI, A ;
PEDRINI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1748-1761
[10]   ADDITION OF 2-SILYLAZOLES TO HETEROARYL CATIONS - SYNTHESIS OF UNSYMMETRICAL AZADIARYLS [J].
DONDONI, A ;
DALLOCCO, T ;
GALLIANI, G ;
MASTELLARI, A ;
MEDICI, A .
TETRAHEDRON LETTERS, 1984, 25 (33) :3637-3640