Studies on novel synthetic methodologies, part 62.: Fe3+-K-10 montmorillonite clay catalyzed friedel-crafts reaction of unactivated Baylis-Hillman adducts:: An efficient stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent

被引:23
作者
Das, B [1 ]
Majhi, A [1 ]
Banerjee, J [1 ]
Chowdhury, N [1 ]
Venkateswarlu, K [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1246/cl.2005.1492
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent has been achieved by employing Friedel-Craft reaction of aromatic compounds with unactivated Baylis-Hillman adducts in the presence of Fe3+-K-10 montmorillonite clay as a heterogeneous catalyst. The catalyst can be recovered and reused.
引用
收藏
页码:1492 / 1493
页数:2
相关论文
共 20 条
[11]   A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate:: factors influencing the yields and stereochemistry of allyl halides [J].
Das, B ;
Banerjee, J ;
Ravindranath, N .
TETRAHEDRON, 2004, 60 (38) :8357-8361
[12]   Organic reactions in water:: An efficient zinc-mediated stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes using unactivated alkyl halides [J].
Das, B ;
Banerjee, J ;
Mahender, G ;
Majhi, A .
ORGANIC LETTERS, 2004, 6 (19) :3349-3352
[13]   Convenient and efficient stereoselective synthesis of (2Z)-2(chloromethyl)alk-2-enoates using iron(III) or indium(III) chloride [J].
Das, B ;
Banerjee, J ;
Ravindranath, N ;
Venkataiah, B .
TETRAHEDRON LETTERS, 2004, 45 (11) :2425-2426
[14]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110
[15]   Palladium-catalyzed cross-coupling of acetates of Bbaylis-Hillman adducts and potassium organotrifluoroborates [J].
Kabalka, GW ;
Venkataiah, B ;
Dong, G .
ORGANIC LETTERS, 2003, 5 (21) :3803-3805
[16]   CATALYSIS OF FRIEDEL-CRAFTS ALKYLATION BY A MONTMORILLONITE DOPED WITH TRANSITION-METAL CATIONS [J].
LASZLO, P ;
MATHY, A .
HELVETICA CHIMICA ACTA, 1987, 70 (03) :577-586
[17]   Friedel-Crafts reaction of the Baylis-Hillman adducts of N-tosylimine derivatives [J].
Lee, HJ ;
Seong, MR ;
Kim, JN .
TETRAHEDRON LETTERS, 1998, 39 (34) :6223-6226
[18]   Baylis-Hillman adducts in rhodium-catalyzed 1,4-additions: unusual reactivity [J].
Navarre, L ;
Darses, S ;
Genet, JP .
CHEMICAL COMMUNICATIONS, 2004, (09) :1108-1109
[19]   A highly convenient, efficient, and selective process for preparation of esters and amides from carboxylic acids using Fe3+-K-10 montmorillonite clay [J].
Srinivas, KVNS ;
Das, B .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :1165-1167
[20]   STUDIES ON PHYTOALEXINS OF THE MORACEAE .5. BROUSSONIN-A AND BROUSSONIN-B NEW PHYTOALEXINS FROM DISEASED PAPER MULBERRY [J].
TAKASUGI, M ;
ANETAI, M ;
MASAMUNE, T ;
SHIRATA, A ;
TAKAHASHI, K .
CHEMISTRY LETTERS, 1980, (03) :339-340