ALKYLPALLADIUM(II) SPECIES - REACTIVE INTERMEDIATES IN A BIS-CYCLIZATION ROUTE TO STRAINED POLYFUSED RING-SYSTEMS

被引：70

作者：

GRIGG, R

SRIDHARAN, V

SUKIRTHALINGAM, S

机构：

[1] School of Chemistry, Leeds University, Leeds

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 31期

关键词：

PALLADIUM; CATALYSIS; CYCLIZATION; STRAINED RING;

D O I：

10.1016/S0040-4039(00)79396-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Alkenyl-allylic and -vinylic acetates or bromides undergo Pd(0) catalysed bis-cyclisation via an initial 5- or 6-exo-trig ring closure generating an alkylpalladium(II) intermediate which reacts further via a 3-, 4- or 5-exo-trig cyclisation onto a proximate alkene or aryl ring generating strained polyfused ring systems stereospecifically.

引用

收藏

页码：3855 / 3858

页数：4

相关论文

共 21 条

[1] 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

[2] CONSTRUCTION OF QUATERNARY CARBON CENTERS BY PALLADIUM-CATALYZED INTRAMOLECULAR ALKENE INSERTIONS - TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOIDS (+/-)-TAZETTINE AND (+/-)-6A-EPIPRETAZETTINE [J].

ABELMAN, MM ;

OVERMAN, LE ;

TRAN, VD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :6959-6964

[3] PALLADIUM CATALYZED TANDEM CYCLIZATION ANION CAPTURE PROCESSES - HYDRIDE ION CAPTURE BY ALKYL-PALLADIUM AND PI-ALLYL-PALLADIUM SPECIES [J].

BURNS, B ;

GRIGG, R ;

RATANANUKUL, P ;

SRIDHARAN, V ;

STEVENSON, P ;

WORAKUN, T .

TETRAHEDRON LETTERS, 1988, 29 (34) :4329-4332

[4] PALLADIUM CATALYZED TANDEM CYCLIZATION ANION CAPTURE PROCESSES - HYDRIDE ION CAPTURE BY VINYLPALLADIUM SPECIES [J].

BURNS, B ;

GRIGG, R ;

SRIDHARAN, V ;

WORAKUN, T .

TETRAHEDRON LETTERS, 1988, 29 (34) :4325-4328

[5] PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF TRIENYL TRIFLATES [J].

CARPENTER, NE ;

KUCERA, DJ ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5846-5848

[6] GROUP-VIII METAL-CATALYZED C-C BOND-FORMING SEQUENCES [J].

CHIUSOLI, GP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 300 (1-2) :57-80

[7] PALLADIUM(II) CATALYZED CONSTRUCTION OF TETRASUBSTITUTED CARBON CENTERS, AND SPIRO-RING AND BRIDGED-RING COMPOUNDS FROM ENAMIDES OF 2-IODOBENZOIC ACIDS [J].

GRIGG, R ;

SRIDHARAN, V ;

STEVENSON, P ;

WORAKUN, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (23) :1697-1699

[8] SEQUENTIAL 1,3-DIPOLAR CYCLOADDITION-PALLADIUM CATALYZED CYCLIZATION - A POWERFUL NEW TACTICAL COMBINATION [J].

GRIGG, R ;

COULTER, T .

TETRAHEDRON LETTERS, 1991, 32 (10) :1359-1362

[9] THE SYNTHESIS OF FUSED RING NITROGEN-HETEROCYCLES VIA REGIOSPECIFIC INTRAMOLECULAR HECK REACTIONS [J].

GRIGG, R ;

SRIDHARAN, V ;

STEVENSON, P ;

SUKIRTHALINGAM, S ;

WORAKUN, T .

TETRAHEDRON, 1990, 46 (11) :4003-4018

[10] PALLADIUM-CATALYZED POLYCYCLISATION-ANION CAPTURE PROCESSES [J].

GRIGG, R ;

DORRITY, MJ ;

MALONE, JF ;

SRIDHARAN, V ;

SUKIRTHALINGAM, S .

TETRAHEDRON LETTERS, 1990, 31 (09) :1343-1346