CYCLOCARBONYLATION OF 1,6-ENYNES PROMOTED BY IRON CARBONYLS

被引：74

作者：

PEARSON, AJ

DUBBERT, RA

机构：

[1] Department of Chemistry, Case Western Researve University, Cleveland

来源：

ORGANOMETALLICS | 1994年 / 13卷 / 05期

关键词：

D O I：

10.1021/om00017a024

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Iron carbonyls have been found to promote the cyclocarbonylation of 1,6-enynes to give cyclopentenones in good yield. The reaction is essentially the same as the intramolecular Pauson-Khand reaction. The best results were obtained using allyl propargyl ethers as substrates. Isomerization of the alkene moiety competes with cyclization in some cases, leading to reduced yields. Stereoselectivity comparable with that obtained in the Pauson-Khand reaction was observed during the cyclization of alkoxy-substituted enynes; this stereoselectivity appears to be kinetic rather than thermodynamic.

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页码：1656 / 1661

页数：6

相关论文

共 18 条

[1] DIASTEREOSELECTIVE ZIRCONOCENE-PROMOTED BICYCLIZATION-CARBONYLATION OF ALLYLICALLY METHYL-SUBSTITUTED ENYNES - SYNTHESIS OF (+)-IRIDOMYRMECIN [J].

AGNEL, G ;

OWCZARCZYK, Z ;

NEGISHI, E .

TETRAHEDRON LETTERS, 1992, 33 (12) :1543-1546

[2] BASE-CATALYZED INTRAMOLECULAR CYCLOADDITIONS OF ALLYL 3-PHENYLPROP-2-YNYL ETHERS AND 4-METHYLPENT-4-EN-2-YNYL PROP-2-YNYL ETHERS [J].

BARTLETT, AJ ;

LAIRD, T ;

OLLIS, WD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (14) :1315-1320

[3] A SIMPLE ORGANOCOBALT MEDIATED SYNTHESIS OF SUBSTITUTED 3-OXABICYCLO[3.3.0]OCT-6-EN-7-ONES [J].

BILLINGTON, DC ;

WILLISON, D .

TETRAHEDRON LETTERS, 1984, 25 (36) :4041-4044

[4]

DOTZ KH, 1985, TETRAHEDRON, V41, P5797

[5]

DOYAMA K, 1988, B CHEM SOC JPN, V61, P4354

[6] REDUCTIVE CYCLIZATION OF ESTER-CONTAINING ENYNES WITH A PRACTICAL TITANOCENE REAGENT - SYNTHESIS OF BICYCLIC CYCLOPENTENONES AND IMINOCYCLOPENTENES [J].

GROSSMAN, RB ;

BUCHWALD, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5803-5805

[7] 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

[8] BIS(CYCLOPENTADIENYL)TETRACARBONYLDIMOLYBDENUM-ALKYNE COMPLEXES MEDIATED [2 + 2 + 1] CYCLOADDITION - THE FORMATION OF 3-SUBSTITUTED CYCLOPENTENONE DERIVATIVES [J].

MUKAI, C ;

UCHIYAMA, M ;

HANAOKA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (14) :1014-1015

[9] METAL-PROMOTED CYCLIZATION .19. NOVEL BICYCLIZATION OF ENYNES AND DIYNES PROMOTED BY ZIRCONOCENE DERIVATIVES AND CONVERSION OF ZIRCONABICYCLES INTO BICYCLIC ENONES VIA CARBONYLATION [J].

NEGISHI, E ;

HOLMES, SJ ;

TOUR, JM ;

MILLER, JA ;

CEDERBAUM, FE ;

SWANSON, DR ;

TAKAHASHI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3336-3346

[10] METAL PROMOTED CYCLIZATION .7. ZIRCONIUM-PROMOTED BICYCLIZATION OF ENYNES [J].

NEGISHI, E ;

HOLMES, SJ ;

TOUR, JM ;

MILLER, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2568-2569