o-bis(allyldimethylsilyl)benzene as a remarkably effective allylation agent for carbonyl compounds with Bu4NF catalyst

被引:22
作者
Asao, N [1 ]
Shibato, A [1 ]
Itagaki, Y [1 ]
Jourdan, F [1 ]
Maruoka, K [1 ]
机构
[1] Hokkaido Univ, Grad Sch Sci, Dept Chem, Sapporo, Hokkaido 060, Japan
关键词
D O I
10.1016/S0040-4039(98)00453-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new type of fluoride ion catalyzed allylation agent, o-bis(allyldimethylsilyl)-benzene (la) and bis(allyldimethylsilyl)methane (Ib), can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equilibrium to complex with Bu4NF by the favorable chelation of bis(silane) toward the fluoride ion. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3177 / 3180
页数:4
相关论文
共 19 条
[1]   TOTAL SYNTHESIS OF (+/-)-FUMAGILLIN [J].
COREY, EJ ;
SNIDER, BB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (07) :2549-&
[2]   MASS-SPECTROMETRIC DETERMINATION OF HEATS OF FORMATION OF SILICON FLUORIDES SIF(G), SIF2(G) AND SIF3(G) [J].
FARBER, M ;
SRIVASTAVA, RD .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1978, 74 :1089-1095
[3]  
Fleming I., 1989, ORG REACTIONS, V37, P57
[4]  
FLEMING L, 1997, CHEM REV, V97, P2063
[5]   SELECTIVE DESILYLATION OF BIS(TRIMETHYLSILYL)ACETYLENES [J].
HOLMES, AB ;
JENNINGSWHITE, CLD ;
SCHULTHESS, AH ;
AKINDE, B ;
WALTON, DRM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (19) :840-842
[6]  
HOSOMI A, 1978, TETRAHEDRON LETT, P3043
[7]   QUATERNARY AMMONIUM ENOLATES AS SYNTHETIC INTERMEDIATES - REGIOSPECIFIC ALKYLATION REACTION OF KETONES [J].
KUWAJIMA, I ;
NAKAMURA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (11) :3257-3258
[8]   FLUORIDE-ION CATALYZED ALDOL REACTION BETWEEN ENOL SILYL ETHERS AND CARBONYL-COMPOUNDS [J].
NAKAMURA, E ;
SHIMIZU, M ;
KUWAJIMA, I ;
SAKATA, J ;
YOKOYAMA, K ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07) :932-945
[9]  
NAKAMURA E, 1976, TETRAHEDRON LETT, P1699
[10]   FLUORIDE CATALYZED ADDITION OF SILYLACETYLENES TO CARBONYL-COMPOUNDS [J].
NAKAMURA, E ;
KUWAJIMA, I .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (08) :498-499