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Volumn 47, Issue 50, 2006, Pages 8911-8915

Highly diastereoselective Staudinger reaction on 5,6-dihydropyrazin-2-(1H)-ones. Synthesis of enantiopure fused oxopiperazino-β-lactams

Author keywords

Lactams; Asymmetric synthesis; Piperazines

Indexed keywords

ACETIC ACID DERIVATIVE; BETA LACTAM DERIVATIVE; PYRAZINE DERIVATIVE;

EID: 33750607003     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.044     Document Type: Article
Times cited : (17)

References (31)
  • 17
    • 0033525683 scopus 로고    scopus 로고
    • Leading references for chiral acid chlorides:
    • Leading references for chiral acid chlorides:. Alcaide B., and Rodríguez-Vicente A. Tetrahedron Lett. 40 (1999) 2005-2006
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2005-2006
    • Alcaide, B.1    Rodríguez-Vicente, A.2
  • 25
    • 33750608683 scopus 로고    scopus 로고
    • note
    • + (100%).
  • 26
    • 33750608358 scopus 로고    scopus 로고
    • note
    • The absolute configuration of C-3 was established by 2D-NOESY of 3f′.
  • 27
    • 33750616488 scopus 로고    scopus 로고
    • note
    • Under basic conditions and long reaction times, 1b undergoes isomerization of the C{double bond, long}N bond to conjugation with the naphthyl group. However, this isomerization is not observed under Staudinger conditions.
  • 28
    • 33750605884 scopus 로고    scopus 로고
    • note
    • Raising the reaction temperature could either prevent formation of the β-lactam or facilitate its cleavage or decomposition.
  • 29
    • 33750633164 scopus 로고    scopus 로고
    • note
    • 2O, H-2/Ar-H (H-8 Naph, 7.94 ppm).
  • 30
    • 33646544385 scopus 로고    scopus 로고
    • For a recent reference dealing with the stereochemistry of the Staudinger reaction, see:
    • For a recent reference dealing with the stereochemistry of the Staudinger reaction, see:. Jiao L., Liang Y., and Xu J. J. Am. Chem. Soc. 128 (2006) 6060-6069
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6060-6069
    • Jiao, L.1    Liang, Y.2    Xu, J.3
  • 31
    • 33750630996 scopus 로고    scopus 로고
    • note
    • + (100%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.