Silver acetate-catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides

N-Metallated azomethine ylides were generated by the reaction of arylidene glycine imines with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides with excellent diastereoselectivity. The configuration of two of the cycloadducts was confirmed by X-ray crystal...

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Bibliographic Details
Published in:Tetrahedron 2005-04, Vol.61 (15), p.3745-3753
Main Authors: Nyerges, Miklós, Bendell, David, Arany, Andrea, Hibbs, David E., Coles, Simon J., Hursthouse, Michael B., Groundwater, Paul W., Meth-Cohn, Otto
Format: Article
Language:English
Subjects:
Amines
Asymmetric
Azomethine ylide
Cycloaddition
Pyrrolidine
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Summary:N-Metallated azomethine ylides were generated by the reaction of arylidene glycine imines with AgOAc and triethylamine. These azomethine ylides undergo cycloaddition to chiral acrylamides with excellent diastereoselectivity. The configuration of two of the cycloadducts was confirmed by X-ray crystallography. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.02.009