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Volumn , Issue 19, 2007, Pages 3199-3205

Synthesis of four-membered ring spiro-β-lactams by epoxide ring-opening

Author keywords

Lactams; Oxygen heterocycles; Regioselectivity; Ring opening; Spiro compounds

Indexed keywords


EID: 34447321351     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601110     Document Type: Article
Times cited : (17)

References (57)
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    • Eds, R. B. Morin, M. Gorman, Academic Press, New York
    • h) Chemistry and Biology of β-Lactam Antibiotics (Eds.: R. B. Morin, M. Gorman), Academic Press, New York, 1982; vol. 1-3.
    • (1982) Chemistry and Biology of β-Lactam Antibiotics , vol.1-3
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    • For spiro-lactam-based CAI inhibitors see: a
    • For spiro-lactam-based CAI inhibitors see: a) J. Clader, Curr. Top. Med. Chem. 2005, 5, 243-256;
    • (2005) Curr. Top. Med. Chem , vol.5 , pp. 243-256
    • Clader, J.1
  • 27
    • 3042709445 scopus 로고    scopus 로고
    • for non-spiro-lactam-based inhibitors: e
    • for non-spiro-lactam-based inhibitors: e) G. S. Singh, Mini-Rev. Med. Chem. 2004, 4, 69-92;
    • (2004) Mini-Rev. Med. Chem , vol.4 , pp. 69-92
    • Singh, G.S.1
  • 32
    • 14344268301 scopus 로고    scopus 로고
    • G. Berti, in Topics in Stereochemistry (Eds.: N. L. Allinger, E. L. Eliel), John Wiley & Sons, New York, 1973, 7, pp. 93-251 and reference cited therein;
    • b) G. Berti, in Topics in Stereochemistry (Eds.: N. L. Allinger, E. L. Eliel), John Wiley & Sons, New York, 1973, vol. 7, pp. 93-251 and reference cited therein;
  • 39
  • 49
    • 0000334646 scopus 로고    scopus 로고
    • Conformations were minimized with the Amber 8.0-Gaussian 03 package; NOESY-1D-DPFGSE is a double-pulsed-field-gradient-spin-echo pulse sequence experiment, see J. Stonehouse, P. Adell, J. Keeler, A. J. Shaka, J. Am. Chem. Soc. 1994, 116, 6037-6038.
    • Conformations were minimized with the Amber 8.0-Gaussian 03 package; NOESY-1D-DPFGSE is a double-pulsed-field-gradient-spin-echo pulse sequence experiment, see J. Stonehouse, P. Adell, J. Keeler, A. J. Shaka, J. Am. Chem. Soc. 1994, 116, 6037-6038.
  • 50
    • 34447317443 scopus 로고    scopus 로고
    • Chemical shifts of epoxides 2 and 6 and products 3, 4, 7 and 8 are reported in Tables A, B, and C in the Supporting Information.
    • Chemical shifts of epoxides 2 and 6 and products 3, 4, 7 and 8 are reported in Tables A, B, and C in the Supporting Information.
  • 55
    • 34447312772 scopus 로고    scopus 로고
    • Initial geometry optimizations were performed with Gaussian 03 - DFT B3LYP/STO-3G2, after which MM geometry optimization with the GAFF (Generalized Amber Force Field) in the sander module of Amber 8.0 was applied.
    • Initial geometry optimizations were performed with Gaussian 03 - DFT B3LYP/STO-3G2, after which MM geometry optimization with the GAFF (Generalized Amber Force Field) in the "sander" module of Amber 8.0 was applied.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.