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Volumn , Issue 6, 2006, Pages 865-868

Intramolecular staudinger ligation towards biaryl-containing lactams

Author keywords

Atropisomerism; Biaryls; Cyclizations; Macrolactams; Ring contractions

Indexed keywords

BIPHENOMYCIN A; LACTAM DERIVATIVE; MACROCYCLIC LACTAM;

EID: 33645784222     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939059     Document Type: Article
Times cited : (14)

References (25)
  • 12
    • 33645759726 scopus 로고    scopus 로고
    • note
    • 3): δ = 31.41 (q, J = 59.0 Hz).
  • 13
    • 33645784577 scopus 로고    scopus 로고
    • note
    • Recrystallization to increase the ee was impossible because the product is a pasty solid.
  • 14
    • 0034733113 scopus 로고    scopus 로고
    • The absolute configuration of 3 was determined by comparison with the known (R)-tert-butyl(hydroxymethyl) methylphosphine borane. The alcohol was converted to the thioacetate in two steps followed by acetyl group removal to give the chiral thiol, see: Nagata, K.; Matsukawa, S.; Imamoto, T. J. Org. Chem. 2000, 65, 4185.
    • (2000) J. Org. Chem. , vol.65 , pp. 4185
    • Nagata, K.1    Matsukawa, S.2    Imamoto, T.3
  • 17
    • 33645771449 scopus 로고    scopus 로고
    • note
    • The boronic acid component for the Suzuki coupling from 7 was prepared by lithium-halogen exchange with n-BuLi and treatment with triethyl borate.
  • 19
    • 0035826370 scopus 로고    scopus 로고
    • ω-Azido acids were obtained from ω-amino acids by a diazotransfer reaction: Lundquist, J. T.; Pelletier, J. C. Org. Lett. 2001, 3, 781.
    • (2001) Org. Lett. , vol.3 , pp. 781
    • Lundquist, J.T.1    Pelletier, J.C.2
  • 20
  • 21
    • 33645763202 scopus 로고    scopus 로고
    • note
    • 13C NMR (100 MHz, MeOD): δ = 175.9, 170.9, 143.1, 143.0, 140.8, 139.7, 135.7, 134.2, 133.9, 132.2, 131.6, 130.7, 128.2, 127.5, 43.8, 41.2, 37.3, 30.5, 29.1, 27.4, 30.0, 19.6.
  • 22
    • 33645793502 scopus 로고    scopus 로고
    • note
    • Attempts to produce 17c via lactamization of the pentafluorophenyl ester analogue of 12c using an aza-Wittig reaction failed.
  • 23
    • 33645753501 scopus 로고    scopus 로고
    • note
    • The atropenantiomers were separated by analytical HPLC analysis using a chiral Daicel OD-H column with heptane-i-PrOH (98:2) as the eluent.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.