CONVENIENT PREPARATIVE METHOD OF ALPHA,BETA-DISUBSTITUTED CYCLOPENTENONE BY ZIRCONIUM PROMOTED INTERMOLECULAR COUPLING OF AN ALKYNE, ETMGBR(OR ETHYLENE) AND CO

Authors
TAKAHASHI T XI ZF NISHIHARA Y HUO SQ KASAI K AOYAGI K DENISOV V NEGISHI E
Citation
T. Takahashi et al., CONVENIENT PREPARATIVE METHOD OF ALPHA,BETA-DISUBSTITUTED CYCLOPENTENONE BY ZIRCONIUM PROMOTED INTERMOLECULAR COUPLING OF AN ALKYNE, ETMGBR(OR ETHYLENE) AND CO, Tetrahedron, 53(27), 1997, pp. 9123-9134
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
27
Year of publication
1997
Pages
9123 - 9134
Database
ISI
SICI code
0040-4020(1997)53:27<9123:CPMOAC>2.0.ZU;2-B
Abstract
Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addit ion of an internal alkyne and subsequent treatment with CO/I-2 gave al pha,beta-disubstituted cyclopentenone in good to high yields. When a c onjugated enyne was used as an alkyne component, alpha-alkenyl cyclope ntenone was selectively formed in 80-89% yields. In the case of 4,6-de cadiyne, alpha-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynytbenzene afforded alpha alpha'-bridged cyc lopentenone compounds in good yields. (C) 1997 Elsevier Science Ltd.