Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5275330 | Tetrahedron Letters | 2007 | 4 Pages |
Abstract
The reaction of α-lithiated-2-alkyl-2-oxazolines 1-Li with aliphatic, aromatic and heteroaromatic N-cumyl nitrones results in the stereoselective formation of N-cumyl-1,6-dioxa-2,9-diazaspiro[4,4]nonanes 3 which equilibrate with the hydroxylamino derivatives 4. Such equilibrating mixtures can be easily transformed into β-amino alkanamides 5 under reductive conditions, whereas acidic hydrolysis with trifluoroacetic acid (TFA) furnishes high yields of β-phenylamino alkanamides 6 via a cumene hydroperoxide-type rearrangement. Derivatives 5 and 6 provide a backbone of potentially useful unnatural β2,2,3-amino acids.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Vito Capriati, Leonardo Degennaro, Saverio Florio, Renzo Luisi,