Indium mediated intramolecular carbocyclization in aqueous media. A facile and stereoselective synthesis of fused alpha-methylene-gamma-butyrolactones

被引:41
作者
Bryan, VJ [1 ]
Chan, TH [1 ]
机构
[1] MCGILL UNIV,DEPT CHEM,MONTREAL,PQ H3A 2K6,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/0040-4039(96)01125-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indium mediated intramolecular carbocyclization in aqueous media gave cis-fused alpha-methylene-gamma-butyrolactones selectively in good yields. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5341 / 5342
页数:2
相关论文
共 18 条
[1]   A CONCISE CHEMICAL SYNTHESIS OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID (KDN) [J].
CHAN, TH ;
LI, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (10) :747-748
[2]   1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].
CHAN, TH ;
LI, CJ ;
LEE, MC ;
WEI, ZY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192
[3]  
CHAN TH, 1995, J CHEM SOC CHEM COMM, P1003
[4]  
CHAN TH, 1995, TETRAHEDRON LETT, V36, P8957
[5]  
CRIPS GT, 1995, TETRAHEDRON, V51, P5831
[6]  
Diana SCH, 1996, SYNLETT, P263
[7]  
GAO J, 1995, J ORG CHEM, V60, P4228
[8]  
GRIECO PA, 1974, J ORG CHEM, V39, P120, DOI 10.1021/jo00915a036
[9]   TIN-MEDIATED AND INDIUM-MEDIATED ALLYLATION IN AQUEOUS-MEDIA - APPLICATION TO UNPROTECTED CARBOHYDRATES [J].
KIM, E ;
GORDON, DM ;
SCHMID, W ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5500-5507
[10]   HIGHLY EFFICIENT CARBONYL ALLYLATION OF 1,3-DICARBONYL COMPOUNDS IN AQUEOUS-MEDIUM [J].
LI, CJ ;
LU, YQ .
TETRAHEDRON LETTERS, 1995, 36 (16) :2721-2724