Diastereoselective Diels-Alder reaction of 5-(indol-2-yl)-pyran-2-one

Authors
Passarella, D Lesma, G Martinelli, M Silvani, A Canto, M Hidalgo, J
Citation
D. Passarella et al., Diastereoselective Diels-Alder reaction of 5-(indol-2-yl)-pyran-2-one, TETRAHEDRON, 56(29), 2000, pp. 5205-5208
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
29
Year of publication
2000
Pages
5205 - 5208
Database
ISI
SICI code
0040-4020(20000714)56:29<5205:DDRO5>2.0.ZU;2-B
Abstract
5-(Indol-2-yl)-pyran-2-one undergoes cycloaddition to electron-poor and ele ctron-rich dienophiles. Lanthanide shift reagents have been shown to be eff icient catalysts for the inverse electron demand Diels-Alder reactions. The bicycloadducts were formed with complete stereoselectivity. Aminolysis of bicycloadducts with primary amines is described. (C) 2000 Elsevier Science Ltd. All rights reserved.