The use of sulfur ylides in the synthesis of substituted indoles

被引:24
作者
Kennedy, AR [1 ]
Taday, MH [1 ]
Rainier, JD [1 ]
机构
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
关键词
D O I
10.1021/ol0162320
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] This letter describes the insertion of rhodium carbenoids into thioindoles, C-10 thioindoles undergo fragmentation-coupling reactions when exposed to rhodium carbenoids. In an analogous fashion, ketoester- and malonate-substituted carbenoids have been found to insert into C-2 thioindoles, In contrast, vinylogous carbenoids were found to alkylate C-2 thioindoles at C-3.
引用
收藏
页码:2407 / 2409
页数:3
相关论文
共 19 条
[1]   DIAZOTRANSFER REACTIONS WITH PARA-ACETAMIDOBENZENESULFONYL AZIDE [J].
BAUM, JS ;
SHOOK, DA ;
DAVIES, HML ;
SMITH, HD .
SYNTHETIC COMMUNICATIONS, 1987, 17 (14) :1709-1716
[2]   MECHANISTIC ASPECTS OF FORMAL [3 + 4] CYCLOADDITIONS BETWEEN VINYLCARBENOIDS AND FURANS [J].
DAVIES, HML ;
CLARK, DM ;
ALLIGOOD, DB ;
EIBAND, GR .
TETRAHEDRON, 1987, 43 (19) :4265-4270
[3]   CARBENOID VERSUS VINYLOGOUS REACTIVITY IN RHODIUM(II)-STABILIZED VINYLCARBENOIDS [J].
DAVIES, HML ;
HU, BH ;
SAIKALI, E ;
BRUZINSKI, PR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4535-4541
[4]   CONVENIENT SYNTHESIS OF VINYLDIAZOMETHANES FROM ALPHA-DIAZO-BETA-KETO ESTERS AND RELATED SYSTEMS [J].
DAVIES, HML ;
HOUGLAND, PW ;
CANTRELL, WR .
SYNTHETIC COMMUNICATIONS, 1992, 22 (07) :971-978
[5]   SYNTHESIS OF (+/-)-FERRUGININE AND (+/-)-ANHYDROECGONINE METHYL-ESTER BY A TANDEM CYCLOPROPANATION COPE REARRANGEMENT [J].
DAVIES, HML ;
SAIKALI, E ;
YOUNG, WB .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5696-5700
[6]  
Davies HML, 1999, EUR J ORG CHEM, V1999, P2459
[7]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[8]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[9]  
Faulkner DJ, 1999, NAT PROD REP, V16, P155
[10]   Recent developments in indole ring synthesis-methodology and applications [J].
Gribble, GW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075