THE CONVERSION OF VINYL TRIFLATES INTO GAMMA'-HYDROXY-ALPHA,BETA-ENONES

被引：43

作者：

ARCADI, A

CACCHI, S

MARINELLI, F

机构：

[1] UNIV LAQUILA,DIPARTIMENTO CHIM INGN CHIM & MAT,V ASSERGI 4,I-67100 LAQUILA,ITALY

[2] UNIV ROMA LA SAPIENZA,DIPARTIMENTO STUDI CHIM & TECNOL SOSTANZE BIOL ATT,I-00185 ROME,ITALY

来源：

TETRAHEDRON | 1993年 / 49卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(01)80412-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl triflates have been converted into gamma'-hydroxy-alpha,beta-enones through their palladium-catalysed coupling with 1-butyn-4-ols followed by the reaction of the obtained 1-hydroxy-3-yn-5-enes in an acidic CH2Cl2/3 N HCl two-phase system in the presence of the n-BuN4Cl/PdCl2 combination. Both the coupling step and the conversion of the carbon-carbon triple bond into the ketonic group have been performed at room temperature. The conversion of vinyl triflates into gamma'-hydroxy-alpha,beta-enones can be carried out through a one-flask process, without the isolation of 1-hydroxy-3-yn-5-enes.

引用

页码：4955 / 4964

页数：10

共 51 条

[1] ARCADI A, 1991, SYNLETT, P409
[2] BETA-VINYL-GAMMA-BUTYROLACTONES VIA THE PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES WITH Z-2-BUTEN-1,4-DIOL
ARCADI, A
BERNOCCHI, E
CACCHI, S
MARINELLI, F
[J]. TETRAHEDRON, 1991, 47 (08) : 1525 - 1540
[3] ARCADI A, 1993, SYNLETT, P65
[4] PALLADIUM-CATALYZED STEREOSELECTIVE HYDROVINYLATION OF DISUBSTITUTED ACETYLENES - PREPARATION OF FUNCTIONALIZED 1,2,4-TRISUBSTITUTED-1,3-DIENES
ARCADI, A
BERNOCCHI, E
BURINI, A
CACCHI, S
MARINELLI, F
PIETRONI, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (26) : 3465 - 3468
[5] ARCADI A, 1992, TETRAHEDRON LETT, V33, P3915
[6] PALLADIUM-CATALYZED REACTION OF VINYL TRIFLATES AND VINYL ARYL HALIDES WITH 4-ALKYNOIC ACIDS - REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF (E)-DELTA-VINYL ARYL-GAMMA-METHYLENE-GAMMA-BUTYROLACTONES
ARCADI, A
BURINI, A
CACCHI, S
DELMASTRO, M
MARINELLI, F
PIETRONI, BR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) : 976 - 982
[7] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES
ARCADI, A
CACCHI, S
MARINELLI, F
[J]. TETRAHEDRON LETTERS, 1989, 30 (19) : 2581 - 2584
[8] ARCADI A, IN PRESS TETRAHEDRON
[9] EASY ACCESS TO 5-(E)-ALKYNYLIDENE-TETRAHYDRO-2-FURANONES BY A PALLADIUM CATALYZED PROCESS
BOUYSSI, D
GORE, J
BALME, G
[J]. TETRAHEDRON LETTERS, 1992, 33 (20) : 2811 - 2814
[10] RAPID AND STEREOSELECTIVE CONSTRUCTION OF DIENEDIYNES RELATED TO THE NEOCARZINOSTATIN CHROMOPHORE
BRUCKNER, R
SCHEUPLEIN, SW
SUFFERT, J
[J]. TETRAHEDRON LETTERS, 1991, 32 (11) : 1449 - 1452

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