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Volumn 48, Issue 49, 2007, Pages 8651-8654

Oxazoline-mediated highly stereoselective synthesis of α,β-substituted-β-aminoalkanamides, potential precursors of unnatural β2,2,3-amino acids

Author keywords

Amino acids; Lithiation; Nitrones; Oxazolines; Peptides

Indexed keywords

BETA AMINO ACID; BETA AMINO ALKANAMIDE DERIVATIVE; BETA PHENYLAMINO ALKANAMIDE DERIVATIVE; N CUMYL 1,6 DIOXA 2,9 DIAZASPIRO[4,4]NONANE DERIVATIVE; N CUMYL NITRONE DERIVATIVE; NITRONE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 35748968501     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.032     Document Type: Article
Times cited : (8)

References (18)
  • 7
    • 35748966365 scopus 로고    scopus 로고
    • note
    • 4) and the solvent evaporated under reduced pressure. The crude mixture was flash chromatographed (silica gel; petroleum ether/AcOEt = 8-9:2-1) to give the N-cumyl-1,6-dioxa-4,7-diazaspiro[4,4]nonanes 3a-l equilibrating with the corresponding N-hydroxy-N-cumyl-2-(oxazolin-2-yl)-alkanamides 4a-l.
  • 10
    • 35748954585 scopus 로고    scopus 로고
    • note
    • spiro ca. 120 ppm) may be distinguished from hydroxylamino forms 4 (C{double bond, long}N ca. 160 ppm).
  • 11
    • 35748960180 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry to compounds 5 and 6 has been determined by NMR experiments and confirmed by an X-ray analysis (see doi:10.1016/j.tetlet.2007.10.035).
  • 12
    • 9444226868 scopus 로고    scopus 로고
    • For an extensive review on β- and γ-amino acids and peptides, see:
    • For an extensive review on β- and γ-amino acids and peptides, see:. Seebach D., Beck A.K., and Bierbaum D.J. Chem. Biodiversity 1 (2004) 1111-1239
    • (2004) Chem. Biodiversity , vol.1 , pp. 1111-1239
    • Seebach, D.1    Beck, A.K.2    Bierbaum, D.J.3
  • 13
    • 35748959575 scopus 로고    scopus 로고
    • note
    • 4, filtered and the volatiles were removed under reduced pressure. Column chromatography (AcOEt/petroleum ether, 1:4) furnished phenylamino alkanamides 6a-i.
  • 16
    • 34047268957 scopus 로고    scopus 로고
    • An anionic carbon to nitrogen phenyl migration has been also reported:
    • An anionic carbon to nitrogen phenyl migration has been also reported:. Theodorou V., Skobridis K., and Karkatsoulis A. Tetrahedron 63 (2007) 4284-4289
    • (2007) Tetrahedron , vol.63 , pp. 4284-4289
    • Theodorou, V.1    Skobridis, K.2    Karkatsoulis, A.3
  • 17
    • 35748932881 scopus 로고    scopus 로고
    • Examples of biological activity of β-amino acid derivatives have been reported; see: Audia, J. E.; Porter, W. J.; Scott, W. L.; Stack, D. R.; Thompson, R. C. Patent WO 01/34571 A1, 2001; Chem. Abstr. 2001, 134, 367191.
  • 18
    • 35748929618 scopus 로고    scopus 로고
    • Camaggi, G.; Filippini, L.; Gusmeroli, M.; Mormile, S.; Signorini, E.; Garavaglia, C. Patent EP 0718280 A2, 1996; Chem. Abstr. 1996, 125, 168644.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.