SILYLATIVE CYCLOCARBONYLATION OF ACETYLENIC BONDS CATALYZED BY RH-4(CO)(12) - AN EASY ACCESS TO BICYCLO[3.3.0]OCTENONE SKELETONS

被引：31

作者：

MATSUDA, I

ISHIBASHI, H

II, N

机构：

[1] Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa, Nagoya

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 02期

关键词：

D O I：

10.1016/0040-4039(94)02182-B

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed cyclopentenone annulation is found in the reaction of two moles of phenylacetylene and (t)BuMe(2)SiH under CO pressure. This type of CO incorporation is applied to the construction of bicyclo[3.3.0]octenone frameworks from 1,6-diynes.

引用

收藏

页码：241 / 244

页数：4

相关论文

共 29 条

[1] TITANOCENE-CATALYZED CONVERSION OF ENYNES TO BICYCLIC CYCLOPENTENONES [J].

BERK, SC ;

GROSSMAN, RB ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4912-4913

[2] RUTHENIUM-CATALYZED REACTION OF 1,6-DIYNES WITH HYDROSILANES AND CARBON-MONOXIDE - A 3RD WAY OF INCORPORATING CO [J].

CHATANI, N ;

FUKUMOTO, Y ;

MURAI, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11614-11615

[3] HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE SILYLFORMYLATION OF ALKYNES UNDER MILD CONDITIONS PROMOTED BY DIRHODIUM(II) PERFLUOROBUTYRATE [J].

DOYLE, MP ;

SHANKLIN, MS .

ORGANOMETALLICS, 1994, 13 (04) :1081-1088

[4] A [W(CO)5.THF]-MEDIATED PAUSON-KHAND REACTION - CYCLIZATIONS OF 1,6-ENYNES VIA A BATCH-CATALYTIC PROTOCOL [J].

HOYE, TR ;

SURIANO, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1154-1156

[5] PALLADIUM-CATALYZED INTRAMOLECULAR ALKYNE CARBON-MONOXIDE ALKENE INSERTION CASCADE FOR SYNTHESIS OF ALPHA-METHYLENECYCLOPENTENONES [J].

IHLE, NC ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :560-563

[6] CATALYTIC VERSION OF THE INTRAMOLECULAR PAUSON-KHAND REACTION [J].

JEONG, N ;

HWANG, SH ;

LEE, YS ;

CHUNG, YK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3159-3160

[7] ORGANOCOBALT COMPLEXES .2. REACTION OF ACETYLENEHEXACARBONYLDICOBALT COMPLEXES, (R1C2R2)CO2(CO)6, WITH NORBORNENE AND ITS DERIVATIVES [J].

KHAND, IU ;

KNOX, GR ;

PAUSON, PL ;

WATTS, WE ;

FOREMAN, MI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (09) :977-981

[8] EFFECT OF COORDINATING LIGANDS ON THE PAUSON-KHAND CYCLOADDITION - TRAPPING OF AN INTERMEDIATE [J].

KRAFFT, ME ;

SCOTT, IL ;

ROMERO, RH ;

FEIBELMANN, S ;

VANPELT, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7199-7207

[9] DICOBALTOCTACARBONYL ALKYNE COMPLEXES AS INTERMEDIATES IN THE SYNTHESIS OF BICYCLO[3.3.0]OCTENONES FOR THE SYNTHESIS OF CORIOLIN AND HIRSUTIC ACID [J].

MAGNUS, P ;

EXON, C ;

ALBAUGHROBERTSON, P .

TETRAHEDRON, 1985, 41 (24) :5861-5869

[10] STEREOSPECIFIC DICOBALT OCTACARBONYL MEDIATED ENYNE CYCLIZATION FOR THE ENANTIOSPECIFIC SYNTHESIS OF A 6A-CARBOCYCLINE ANALOG [J].

MAGNUS, P ;

BECKER, DP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (24) :7495-7498