BETA-VINYL-GAMMA-BUTYROLACTONES VIA THE PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES WITH Z-2-BUTEN-1,4-DIOL

被引：33
作者：
ARCADI, A
BERNOCCHI, E
CACCHI, S
MARINELLI, F
机构：
[1] UNIV LAQUILA,DIPARTIMENTO CHIM INGN CHIM MAT,VIA ASSERGI 4,I-67100 LAQUILA,ITALY
[2] UNIV ROMA LA SAPIENZA,DIPARTIMENTO CHIM & TECNOL SOSTANZE BIOLOGICAMENTE ATTIVE,I-00185 ROME,ITALY
来源：
TETRAHEDRON | 1991年 / 47卷 / 08期
关键词：
D O I：
10.1016/S0040-4020(01)86427-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol affords beta-vinyl-gamma-butyrolactols (4-vinyl-2-hydroxy-tetrahydrofurans) which are converted into the corresponding beta-vinyl-gamma-butyrolactones by a smooth oxidation with Ag2CO3 on celite. Preparation of beta-substituted-gamma-butyrolactones can be performed without the isolation of the intermediate gamma-butyrolactols, thus simplifying the procedure and usually with higher overall yields. The outcome of the palladium-catalysed formation of beta-substituted-gamma-butyrolactols strongly depends on the nature of the added base. Best results are obtained by using NaHCO3 or K2CO3 in the presence of n-Bu4NCl or TEBA.
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页码：1525 / 1540
页数：16
相关论文
共 62 条
[1]   CONJUGATE ADDITION VS VINYLIC SUBSTITUTION IN PALLADIUM-CATALYZED REACTION OF ARYL HALIDES WITH BETA-SUBSTITUTED-ALPHA,BETA-ENONES AND BETA-SUBSTITUTED-ALPHA,BETA-ENALS [J].
AMORESE, A ;
ARCADI, A ;
BERNOCCHI, E ;
CACCHI, S ;
CERRINI, S ;
FEDELI, W ;
ORTAR, G .
TETRAHEDRON, 1989, 45 (03) :813-828
[2]   REGIOSELECTIVE PALLADIUM-CATALYZED ARYLATION OF VINYL ETHERS WITH 4-NITROPHENYL TRIFLATE - CONTROL BY ADDITION OF HALIDE-IONS [J].
ANDERSSON, CM ;
HALLBERG, A .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (09) :2112-2114
[3]   STUDIES ON THE SYNTHESES OF SESQUITERPENE LACTONES .10. IMPROVED SYNTHESES OF (+)-TUBERIFERIN AND THE RELATED ALPHA-METHYLENE GAMMA-LACTONES AND THEIR BIOLOGICAL-ACTIVITIES [J].
ANDO, M ;
WADA, T ;
KUSAKA, H ;
TAKASE, K ;
HIRATA, N ;
YANAGI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4792-4796
[4]   THE REACTION OF ALKYL 4-HYDROXY-2-ALKYNOATES AND 4-HYDROXY-2-ALKYN-1-ONES WITH PALLADIUM TRIBUTYLAMMONIUM FORMATE AND WITH TRIBUTYLAMINE - PREPARATION OF 1,4-DICARBONYL COMPOUNDS [J].
ARCADI, A ;
CACCHI, S ;
MARINELLI, F ;
MISITI, D .
TETRAHEDRON LETTERS, 1988, 29 (12) :1457-1460
[5]   THE REACTION OF ARYL IODIDES WITH HINDERED ALPHA,BETA,GAMMA,DELTA-DIENONES IN THE PRESENCE OF THE [PD(OAC)2(PPH3)2]-TRIALKYLAMMONIUM FORMATE REAGENT [J].
ARCADI, A ;
MARINELLI, F ;
CACCHI, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 312 (02) :C27-C32
[6]   AN EFFICIENT ROUTE FOR THE STEREOSELECTIVE CONVERSION OF KETONES INTO 3-CARBONS HOMOLOGATED PRIMARY E-ALLYLAMINES - THE PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES WITH N,N-DI-TERT-BUTOXYCARBONYL-N-ALLYLAMINE [J].
ARCADI, A ;
BERNOCCHI, E ;
CACCHI, S ;
CAGLIOTI, L ;
MARINELLI, F .
TETRAHEDRON LETTERS, 1990, 31 (17) :2463-2466
[7]   THE PALLADIUM-CATALYZED REDUCTIVE ADDITION OF ARYL IODIDES TO PROPARGYL ALCOHOLS - A ROUTE TO GAMMA,GAMMA-DIARYL ALLYLIC ALCOHOLS [J].
ARCADI, A ;
CACCHI, S ;
MARINELLI, F .
TETRAHEDRON, 1985, 41 (22) :5121-5131
[8]  
ARCADI A, 1990, SYNLETT, P47
[9]   THE PALLADIUM-TRIBUTYLAMMONIUM FORMATE REAGENT IN THE STEREOSELECTIVE HYDROGENATION, AND STEREOSELECTIVE AND REGIOSELECTIVE HYDROARYLATION OF ALKYL 4-HYDROXY-2-ALKYNOATES - A ROUTE TO SUBSTITUTED BUTENOLIDES [J].
ARCADI, A ;
BERNOCCHI, E ;
BURINI, A ;
CACCHI, S ;
MARINELLI, F ;
PIETRONI, B .
TETRAHEDRON, 1988, 44 (02) :481-490
[10]  
ARCADI A, 1986, SYNTHESIS-STUTTGART, P749
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