A NEW [2+3] ANNULATION FOR HIGHLY FUNCTIONALIZED DIHYDROFURANS VIA C-C BOND FORMATION

被引:13
作者
HUDLICKY, T
BARBIERI, G
机构
[1] Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg
关键词
D O I
10.1021/jo00015a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unique low-temperature rearrangement of silyl enol ether terminated oxiranes, prepared by the addition of the dienolate anion of ethyl 2-bromo-4-siloxy-crotonate to aldehydes, has been implemented for the synthesis of functionalized dihydrofurans.
引用
收藏
页码:4598 / 4600
页数:3
相关论文
共 38 条
[2]   APPLICATION OF ALLENYLSILANES IN [3 + 2] ANNULATION APPROACHES TO OXYGEN AND NITROGEN-HETEROCYCLES [J].
DANHEISER, RL ;
KWASIGROCH, CA ;
TSAI, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7233-7235
[3]   A NEW SYNTHESIS OF SUBSTITUTED FURANS [J].
DANHEISER, RL ;
STONER, EJ ;
KOYAMA, H ;
YAMASHITA, DS ;
KLADE, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4407-4413
[4]   A CONCISE AND STEREOSELECTIVE ROUTE TO THE PREDOMINANT STEREOCHEMICAL PATTERN OF THE TETRAHYDROPYRANOID ANTIBIOTICS - AN APPLICATION TO INDANOMYCIN [J].
DANISHEFSKY, SJ ;
DENINNO, S ;
LARTEY, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2082-2089
[5]   THE EPOXYHEXENYNE - VINYLFURAN TRANSFORMATION - EVIDENCE FOR CARBENE INTERMEDIATES [J].
EBERBACH, W ;
ROSER, J .
TETRAHEDRON LETTERS, 1987, 28 (24) :2685-2688
[6]   BUTADIENYLOXIRANE-DIHYDROOXEPINE ISOMERIZATION - RING EXPANSION REACTIONS OF STERICALLY FIXED AND BENZOANNELATED EPOXYHEXADIENES BY 1,7-ELECTROCYCLIZATION OF CONJUGATED CARBONYL YLIDES [J].
EBERBACH, W ;
TROSTMANN, U .
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (10) :4035-4058
[7]   VINYLOXIRANE DIHYDROFURAN ISOMERIZATION - MECHANISM AND SYNTHETIC USE [J].
EBERBACH, W ;
BURCHARDT, B .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (11) :3665-3698
[8]   TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206 [J].
EVANS, DA ;
BENDER, SL ;
MORRIS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2506-2526
[9]  
HUDICKY T, 1989, J AM CHEM SOC, V111, P6691
[10]  
HUDLICKLY T, 1991, COMPREHENSIVE ORGANI, V5, pCH8