FORMATION OF CYCLOPENTANES DURING HECK REACTIONS

被引:30
作者
FOURNET, G
BALME, G
GORE, J
机构
[1] Laboratoire de Chimie Organique 1, associé au CNRS, Université Claude Bernard, 69622 Villeurbanne, 43 Bd du
关键词
D O I
10.1016/S0040-4020(01)90073-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Heck reaction of alkenes bearing in δ position an enolate of β-diester, βketo ester or β-sulfonyl ester leads to cyclopentanes issued from the intramolecular displacement of the carbone sp3-palladium bond by this enolate. This cyclisation is not observed when the enolate is in β or ε position or in the case of a δ-ethylenic amine and βelimination products are only obtained. © 1990.
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收藏
页码:7763 / 7774
页数:12
相关论文
共 29 条
[1]   PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF DIENYL ARYL IODIDES [J].
ABELMAN, MM ;
OVERMAN, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2328-2329
[2]   INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].
ABELMAN, MM ;
OH, T ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133
[3]   DESICCANT EFFICIENCY IN SOLVENT AND REAGENT DRYING .7. ALCOHOLS [J].
BURFIELD, DR ;
SMITHERS, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2420-2422
[4]   DESICCANT EFFICIENCY IN SOLVENT DRYING .3. DIPOLAR APROTIC-SOLVENTS [J].
BURFIELD, DR ;
SMITHERS, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3966-3968
[5]   REGIOSPECIFIC PALLADIUM CATALYZED TANDEM CYCLISATION-ANION CAPTURE PROCESSES - STEREOSPECIFIC GROUP TRANSFER FROM ORGANOZINC AND ORGANOBORON REAGENTS [J].
BURNS, B ;
GRIGG, R ;
SRIDHARAN, V ;
STEVENSON, P ;
SUKIRTHALINGAM, S ;
WORAKUN, T .
TETRAHEDRON LETTERS, 1989, 30 (09) :1135-1138
[6]   EFFICIENT PALLADIUM-MEDIATED SYNTHESIS OF A SPIROCYCLIC MODEL FOR FREDERICAMYCIN-A [J].
CIUFOLINI, MA ;
BROWNE, ME .
TETRAHEDRON LETTERS, 1987, 28 (02) :171-174
[7]   TOTAL SYNTHESIS OF (+/-)-DASYCARPIDONE, (+/-)-EPIDASYCARPIDONE, AND (+/-)-EPIULEINE [J].
DOLBY, LJ ;
BIERE, H .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3843-&
[8]  
FOURMET G, 1986, TETRAHEDRON LETT, V27, P3855
[9]   INTRAMOLECULAR NUCLEOPHILIC-ATTACK OF ORGANOPALLADIUM COMPOUNDS RESULTING FROM CARBOPALLADATION OF ALKYLIDENECYCLOPROPANES [J].
FOURNET, G ;
BALME, G ;
GORE, J .
TETRAHEDRON LETTERS, 1987, 28 (39) :4533-4536
[10]   CARBOPALLADATION OF ALKYLIDENE CYCLOPROPANES .2. INTRAMOLECULAR CAPTURE OF THE ORGANOPALLADIC INTERMEDIARY [J].
FOURNET, G ;
BALME, G ;
BARIEUX, JJ ;
GORE, J .
TETRAHEDRON, 1988, 44 (18) :5821-5832