PALLADIUM-CATALYZED INTRAMOLECULAR ALKYNE CARBON-MONOXIDE ALKENE INSERTION CASCADE FOR SYNTHESIS OF ALPHA-METHYLENECYCLOPENTENONES

被引：51

作者：

IHLE, NC ^{[1
]}

HEATHCOCK, CH ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY, DEPT CHEM, BERKELEY, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 03期

关键词：

D O I：

10.1021/jo00055a006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the construction of alpha-methylenecyclopentenones fused to five-membered rings using a palladium catalyst is reported. The procedure involves the formation of pi-allylpalladium intermediates that undergo sequential intramolecular alkyne insertion, carbon monoxide insertion, intramolecular alkene insertion, and beta-hydride elimination. Examples of the cyclization are seen in eq 2 and Scheme III.

引用

页码：560 / 563

页数：4

共 24 条

[21] N-OXIDE PROMOTED PAUSON-KHAND CYCLIZATIONS AT ROOM-TEMPERATURE
SHAMBAYATI, S
CROWE, WE
SCHREIBER, SL
[J]. TETRAHEDRON LETTERS, 1990, 31 (37) : 5289 - 5292
[22] ADSORPTION EFFECTS ON THE EFFICIENCY OF COBALT-MEDIATED CYCLIZATIONS OF ALLYLPROPARGYL ETHERS INTO DERIVATIVES OF 3-OXABICYCLO[3.3.0]OCT-5-EN-7-ONE
SIMONIAN, SO
SMIT, WA
GYBIN, AS
SHASHKOV, AS
MIKAELIAN, GS
TARASOV, VA
IBRAGIMOV, II
CAPLE, R
FROEN, DE
[J]. TETRAHEDRON LETTERS, 1986, 27 (11) : 1245 - 1248
[23] CHEMISTRY OF DIBENZYLIDENEACETONE-PALLADIUM(0) COMPLEXES .1. NOVEL TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(SOLVENT) COMPLEXES AND THEIR REACTIONS WITH QUINONES
UKAI, T
KAWAZURA, H
ISHII, Y
BONNET, JJ
IBERS, JA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 65 (02) : 253 - 266
[24] YOO SE, 1990, TETRAHEDRON LETT, V31, P6877

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