Convergent regiodirected assembly of 2,3-disubstituted furans

Authors
Mendez-Andino, J Paquette, LA
Citation
J. Mendez-andino et La. Paquette, Convergent regiodirected assembly of 2,3-disubstituted furans, ORG LETT, 2(25), 2000, pp. 4095-4097
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
25
Year of publication
2000
Pages
4095 - 4097
Database
ISI
SICI code
1523-7060(200012)2:25<4095:CRAO2F>2.0.ZU;2-Z
Abstract
[GRAPHICS] The conjugate addition of organocopper reagents to alpha,beta -unsaturated enones results in the regiospecific generation of enolate anions, which can be made to undergo the aldol reaction with (tetrahydropyranyloxy)acetaldeh yde under zinc chloride catalysis. Treatment of the resulting product with p-toluenesulfonic acid in THF affords the targeted 2,3-disubstituted furan.