Diastereoselective Diels–Alder Reaction of 5-(Indol-2-yl)-pyran-2-one

5-(Indol-2-yl)-pyran-2-one undergoes cycloaddition to electron-poor and electron-rich dienophiles. Lanthanide shift reagents have been shown to be efficient catalysts for the inverse electron demand Diels–Alder reactions. The bicycloadducts were formed with complete stereoselectivity. Aminolysis of...

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Bibliographic Details
Published in:Tetrahedron 2000-07, Vol.56 (29), p.5205-5208
Main Authors: Passarella, Daniele, Lesma, Giordano, Martinelli, Marisa, Silvani, Alessandra, Cantò, Margalida, Hidalgo, Josè
Format: Article
Language:English
Subjects:
cycloaddition
indoles
lanthanides
pyrones
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Summary:5-(Indol-2-yl)-pyran-2-one undergoes cycloaddition to electron-poor and electron-rich dienophiles. Lanthanide shift reagents have been shown to be efficient catalysts for the inverse electron demand Diels–Alder reactions. The bicycloadducts were formed with complete stereoselectivity. Aminolysis of bicycloadducts with primary amines is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00183-6