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Volumn , Issue 9, 2005, Pages 1765-1776

A new diastereoselective synthetic approach to the enantiopure peptidomimetic scaffold 2-oxo-1-azabicyclo[4.4.0]decane

Author keywords

Asymmetric synthesis; C C coupling; Peptidomimetics; Synthetic methods

Indexed keywords


EID: 18744364708     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400709     Document Type: Article
Times cited : (13)

References (66)
  • 38
    • 0032564612 scopus 로고    scopus 로고
    • and refs.[39-41]
    • For some synthetic applications of 6, see: Q. Wang, N. A. Sasaki, P. Potier, Tetrahedron 1998, 54, 15759-15780 and refs.[39-41]
    • (1998) Tetrahedron , vol.54 , pp. 15759-15780
    • Wang, Q.1    Sasaki, N.A.2    Potier, P.3
  • 46
    • 18744392598 scopus 로고    scopus 로고
    • note
    • The following columns were tried without success: Symmetry, Symmetry Shield and X-Terra from Waters; Hypercarb and Aquastar from Thermo Electron; Nucleodex β-PM from Macherey-Nagel.
  • 47
    • 18744364982 scopus 로고    scopus 로고
    • note
    • Deuterated chloroform, acetone, acetonitrile, benzene, and methanol were tried.
  • 50
    • 18744411318 scopus 로고    scopus 로고
    • note
    • Relative to the fluorotrichloromethane internal reference at δ = 0 ppm.
  • 51
    • 18744374964 scopus 로고    scopus 로고
    • note
    • 19F NMR spectroscopy.
  • 55
    • 18744371347 scopus 로고    scopus 로고
    • note
    • All NOESY experiments were conducted on a 400 MHz Bruker apparatus. Deuterated chloroform was used for 23 and 28a and deuterated methanol for 28b.
  • 58
    • 18744393485 scopus 로고    scopus 로고
    • note
    • 13C NMR spectroscopy.
  • 59
    • 0001269705 scopus 로고    scopus 로고
    • and refs. [60] and [61]
    • Good stereoselectivities for the reductive desulfonylation of quaternary centers were observed from α-cyclic sulfones see, for example: S. A. Lomenzo, A. L. Bradley, N. Zhu, C. L. Klein, M. L. Trudell, J. Heterocycl. Chem. 1997, 34, 1139-1146 and refs. [60] and [61].
    • (1997) J. Heterocycl. Chem. , vol.34 , pp. 1139-1146
    • Lomenzo, S.A.1    Bradley, A.L.2    Zhu, N.3    Klein, C.L.4    Trudell, M.L.5
  • 66
    • 18744416068 scopus 로고    scopus 로고
    • note
    • Purchased from Acros Organics as a 50% slurry in water.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.