Domino "[3+3]-cyclization-homo-Michael" reactions of 1,3-bissilyl enol ethers with 1,1-diacylcyclopropanes

被引:44
作者
Bose, G
Nguyen, VTH
Ullah, E
Lahiri, S
Görls, H
Langer, P
机构
[1] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany
[2] Univ Jena, Inst Anorgan & Analyt Chem, D-07740 Jena, Germany
关键词
D O I
10.1021/jo0485278
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Lewis acid mediated domino " [3+3] -cyclization-homo-Michael" reaction of 1,3-bissilyl enol ethers with 1,1-diacylcyclopropanes allows an efficient one-pot synthesis of functionalized salicylates containing a halogenated side chain. A great variety of substitution patterns could be realized by variation of the starting materials and of the Lewis acid. The mechanism of the domino process was studied.
引用
收藏
页码:9128 / 9134
页数:7
相关论文
共 36 条
[1]  
[Anonymous], 2015, Acta Crystallogr., V71, P3
[2]   SESQUITERPENES FROM PITYROGRAMMA-CALOMELANOS [J].
BARDOUILLE, V ;
MOOTOO, BS ;
HIROTSU, K ;
CLARDY, J .
PHYTOCHEMISTRY, 1978, 17 (02) :275-277
[3]  
Battiste M.A., 1987, CHEM CYCLOPROPYL GRO, V1, P255
[4]  
Bednarski M.D., 1991, COMPREHENSIVE ORGANI, V2, P661, DOI DOI 10.1016/B978-0-08-052349-1.00044-5
[5]   Synthesis and reactivity of 1-hydroxyspiro[2.5]cyclooct-4-en-3-ones [J].
Bose, G ;
Langer, P .
TETRAHEDRON LETTERS, 2004, 45 (20) :3861-3863
[6]   CHEMISTRY OF ENOL SILYL ETHERS - A GENERAL-SYNTHESIS OF 3-HYDROXYHOMOPHTHALATES AND A BIOMIMETIC SYNTHESIS OF SCLERIN .12. [J].
BROWNBRIDGE, P ;
CHAN, TH ;
BROOK, MA ;
KANG, GJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (04) :688-693
[7]   A BIOMIMETIC SYNTHESIS OF DELTA-1-TETRAHYDROCANNABINOL [J].
CHAN, TH ;
CHALY, T .
TETRAHEDRON LETTERS, 1982, 23 (29) :2935-2938
[8]  
CHAN TH, 1979, J CHEM SOC CHEM COMM, P578, DOI 10.1039/c39790000578
[9]   CHEMISTRY OF ENOL SILYL ETHERS .5. A NOVEL CYCLOAROMATIZATION REACTION - REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED METHYL SALICYLATES [J].
CHAN, TH ;
BROWNBRIDGE, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (10) :3534-3538
[10]   ELECTROPHILIC CYCLOPROPANES IN ORGANIC-SYNTHESIS [J].
DANISHEFSKY, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (02) :66-72