Title of article :
Oxazoline-mediated highly stereoselective synthesis of α,β-substituted-β-aminoalkanamides, potential precursors of unnatural β2,2,3-amino acids
Author/Authors :
Capriati، نويسنده , , Vito and Degennaro، نويسنده , , Leonardo and Florio، نويسنده , , Saverio and Luisi، نويسنده , , Renzo، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2007
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.
Keywords :
Oxazolines , amino acids , Peptides , Nitrones , lithiation
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters