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EnglishThe reaction of alpha-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 beta-amino alkanamides 5 under reductive conditions, whereas acidic hydrolysis with trifluoroacetic acid (TFA) furnishes high yields of beta-phenylamino alkanamides 6 via a cumene hydroperoxide- type rearrangement. Derivatives 5 and 6 provide a backbone of potentially useful unnatural beta-2,2,3-amino acids.
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| Titolo: | Oxazoline-mediated highly stereoselective synthesis of alpha,beta-substituted-beta-aminoalkanamides, potential precursors of unnatural beta2,2,3-amino acids |
| Autori: | |
| Data di pubblicazione: | 2007 |
| Rivista: | |
| Citazione: | Oxazoline-mediated highly stereoselective synthesis of alpha,beta-substituted-beta-aminoalkanamides, potential precursors of unnatural beta2,2,3-amino acids / CAPRIATI V; DEGENNARO; L; FLORIO; S; LUISI; R. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 48(2007), pp. 8651-8654. |
| Abstract: | The reaction of alpha-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 beta-amino alkanamides 5 under reductive conditions, whereas acidic hydrolysis with trifluoroacetic acid (TFA) furnishes high yields of beta-phenylamino alkanamides 6 via a cumene hydroperoxide- type rearrangement. Derivatives 5 and 6 provide a backbone of potentially useful unnatural beta-2,2,3-amino acids. |
| Handle: | http://hdl.handle.net/11586/134700 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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