Intriguing formal [2+3] cycloaddition promoted by a hypervalent iodine reagent

被引:53
作者
Berard, Didier [1 ]
Giroux, Marc-Andre [1 ]
Racicot, Leanne [1 ]
Sabot, Cyrille [1 ]
Canesi, Sylvain [1 ]
机构
[1] Univ Quebec, Lab Methodol & Synth Prod Nat, Montreal, PQ H3C 3P8, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/j.tet.2008.05.114
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of various substituted phenols in the presence of iodobenzene diacetate, perfluorinated alcohols and furan, allylsilanes or cyclic enol ethers promotes an oxidative annulation process in moderate to useful yields. In only one step, this method produces different heterocyclic rings such as dihydrofuranobenzofurans, tetrahydrofuranobenzofurans, tetra hydropyranofurans, and dihydrobenzofurans. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7537 / 7544
页数:8
相关论文
共 118 条
[101]   PALLADIUM CATALYZED OXYCARBONYLATION OF 4-PENTEN-1,3-DIOLS - EFFICIENT STEREOSELECTIVE SYNTHESIS OF CIS 3-HYDROXYTETRAHYDROFURAN 2-ACETIC ACID LACTONES [J].
TAMARU, Y ;
KOBAYASHI, T ;
KAWAMURA, S ;
OCHIAI, H ;
HOJO, M ;
YOSHIDA, Z .
TETRAHEDRON LETTERS, 1985, 26 (27) :3207-3210
[102]  
TAMURA E, 1994, SYNLETT, P609
[103]   HYPERVALENT IODINE OXIDATION OF PARA-ALKOXYPHENOLS AND RELATED-COMPOUNDS - A GENERAL-ROUTE TO PARA-BENZOQUINONE MONOACETALS AND SPIRO LACTONES [J].
TAMURA, Y ;
YAKURA, T ;
HARUTA, J ;
KITA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3927-3930
[104]   Efficient oxidative biaryl coupling reaction of phenol ether derivatives using hypervalent iodine(III) reagents [J].
Tohma, H ;
Morioka, H ;
Takizawa, S ;
Arisawa, M ;
Kita, Y .
TETRAHEDRON, 2001, 57 (02) :345-352
[105]   A CATIONIC MODEL OF THE CHAIN-BRANCHING STEP IN AFLATOXIN BIOSYNTHESIS [J].
TOWNSEND, CA ;
DAVIS, SG ;
KOREEDA, M ;
HULIN, B .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5428-5430
[106]   SYNTHESIS OF AVERUFIN AND ITS ROLE IN AFLATOXIN-B1 BIOSYNTHESIS [J].
TOWNSEND, CA ;
CHRISTENSEN, SB ;
DAVIS, SG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (04) :839-861
[107]   REACTION MODELS OF THE OXIDATIVE REARRANGEMENT OF AVERUFIN TO 1'-HYDROXYVERSICOLORONE - THE 1ST STEP IN DIHYDROBISFURAN FORMATION IN AFLATOXIN BIOSYNTHESIS [J].
TOWNSEND, CA ;
ISOMURA, Y ;
DAVIS, SG ;
HODGE, JA .
TETRAHEDRON, 1989, 45 (08) :2263-2276
[108]   BISFURAN FORMATION IN AFLATOXIN BIOSYNTHESIS - THE ROLE OF VERSICONAL ACETATE [J].
TOWNSEND, CA ;
CHRISTENSEN, SB ;
DAVIS, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) :6154-6155
[109]   HYDROXYVERSICOLORONE - SYNTHESIS AND INCORPORATION OF A NEW INTERMEDIATE IN AFLATOXIN BIOSYNTHESIS [J].
TOWNSEND, CA ;
WHITTAMORE, PRO ;
BROBST, SW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (11) :726-728
[110]   Palladium catalyzed kinetic and dynamic kinetic asymmetric transformations of γ-acyloxybutenolides.: Enantioselective total synthesis of (+)-aflatoxin B1 and B2a [J].
Trost, BM ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :3090-3100