UNSATURATED SULFOXIDES IN ORGANIC-SYNTHESIS - A NEW GENERAL FURAN SYNTHESIS

被引:21
作者
CHAN, WH
LEE, AWM
CHAN, ETT
机构
[1] Department of Chemistry, Hong Kong Baptist College, Kowloon
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 08期
关键词
D O I
10.1039/p19920000945
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Furans have been efficiently synthesised by a three-step reaction sequence. Michael addition of keto esters to alkenyl sulfoxides followed by Pummerer rearrangement afforded the cyclic intermediates 11 in good yield. Treatment of the latter with 2-chloroperoxybenzoic acid led by oxidation and syn-elimination of the corresponding sulfoxide, to substituted furans.
引用
收藏
页码:945 / 946
页数:2
相关论文
共 15 条
[1]   ELIMINATION-ADDITION .22. ADDITION OF ENOLATES TO ALLENIC SULFONIUM SALTS - NEW GENERAL FURAN SYNTHESIS [J].
BATTY, JW ;
HOWES, PD ;
STIRLING, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (01) :65-68
[2]  
BISAGNI E, 1971, B SOC CHIM FR, P4041
[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]   RECENT ADVANCES IN FURAN CHEMISTRY .1. [J].
DEAN, FM .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1982, 30 :167-238
[5]  
DEAN FM, 1982, ADV HETEROCYCL CHEM, V31, P237
[6]   SYNTHESIS OF SUBSTITUTED FURANS BY PALLADIUM-CATALYZED CYCLIZATION OF ACETYLENIC KETONES [J].
FUKUDA, Y ;
SHIRAGAMI, H ;
UTIMOTO, K ;
NOZAKI, H .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5816-5819
[7]   ORGANIC SYNTHESIS BY PUMMERER REACTION .2. SYNTHESIS OF ALPHA-HYDROXY ACID-DERIVATIVES FROM BETA-KETO SULFOXIDES [J].
IRIUCHIJIMA, S ;
MANIWA, K ;
TSUCHIHASHI, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :596-596
[8]  
KANO S, 1979, J CHEM SOC CHEM COMM, P238
[9]   CHIRAL ACETYLENIC SULFOXIDE IN ALKALOID SYNTHESIS - TOTAL SYNTHESIS OF (R)-(+)-CARNEGINE [J].
LEE, AWM ;
CHAN, WH ;
LEE, YK .
TETRAHEDRON LETTERS, 1991, 32 (47) :6861-6864
[10]   ACETYLENIC SULFOXIDES IN ORGANIC-SYNTHESIS - DIELS-ALDER REACTIONS [J].
LEE, AWM ;
CHAN, WH ;
WONG, MS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) :1585-1586