Synthesis of functionalized benzopyrans by sequential [3+3]-cyclization-Williamson reactions of 1.3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes

被引:19
作者
Nguyen, VH [1 ]
Langer, P [1 ]
机构
[1] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany
关键词
benzopyrans; cyclizations; ethers; lewis acids; silyl enol ethers;
D O I
10.1016/j.tetlet.2004.12.009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Functionalized benzopyrans were regioselectively prepared by [3+3]-cyclization of 1,3-bis(trimethylsilyloxy)-7-chloro-hepta-1,3-dienes with 3-silyloxy-2-eno-1-ones and Subsequent intramolecular Williamson reactions of the salicylates thus formed. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:815 / 817
页数:3
相关论文
共 29 条
[1]  
BOSE G, 2004, IN PRESS J ORG CHEM
[2]   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
[3]  
CHAN TH, 1979, J CHEM SOC CHEM COMM, P578, DOI 10.1039/c39790000578
[4]   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
[5]   CONVERSION OF ALKYL ACETATES TO (SILOXYMETHYLENE)ALKANES BY CO2(CO)8-CATALYZED REACTION WITH A HYDROSILANE AND CARBON-MONOXIDE [J].
CHATANI, N ;
MURAI, S ;
SONODA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (05) :1370-1372
[6]   COBALT CARBONYL CATALYZED-REACTIONS OF ESTERS AND LACTONES WITH HYDROSILANE AND CARBON-MONOXIDE - A NOVEL SYNTHETIC METHOD FOR THE INTRODUCTION OF THE SILOXYMETHYLIDENE GROUP [J].
CHATANI, N ;
FUJII, S ;
YAMASAKI, Y ;
MURAI, S ;
SONODA, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7361-7373
[7]   Synthesis of functionalized acetophenones by [3+3] cyclizations of 1,3-bis-silyl enol ethers with 2-acetyl-3-silyloxyalk-2-en-1-ones [J].
Dede, R ;
Langer, P .
TETRAHEDRON LETTERS, 2004, 45 (50) :9177-9179
[8]   β-Siloxy unsaturated nitriles:: stereodivergent cyclizations to cis- and trans-decalins [J].
Fleming, FF ;
Shook, BC ;
Jiang, T ;
Steward, OW .
TETRAHEDRON, 2003, 59 (06) :737-745
[9]  
HAMBLY GF, 1986, TETRAHEDRON LETT, V27, P2562
[10]  
Hydrio J, 1997, SYNTHESIS-STUTTGART, P68