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Volumn 64, Issue 1, 1999, Pages 252-265

Systematic synthesis of multifluorinated α,α-difluoro-γ-lactones through intramolecular radical cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA,ALPHA DIFLUORO GAMMA LACTONE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033534668     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982035b     Document Type: Article
Times cited : (57)

References (103)
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    • Tozer, M.J.1    Herpin, T.F.2
  • 3
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    • Synthetic methods for difluoromethyl compounds has progressed extensively recently. For examples, see. (a) Percy, J. M.; Wilkes, R. D. Tetrahedron 1997, 53, 14749.
    • (1997) Tetrahedron , vol.53 , pp. 14749
    • Percy, J.M.1    Wilkes, R.D.2
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    • Several examples have been reported of the formation of five-or six-membered ring compounds that possess difluoromethylene moiety using a radical process: (d) Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1121
    • Barth, F.1    O-Yang, C.2
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    • note
    • CS Chem3D Pro was employed to calculate the steric energy of four isomers of 3a. Calculations suggested that both (4,5-cis)-isomers are sterically more stable than corresponding (4,5-trans)-isomers; these well agreed with the experimental results.
  • 77
    • 0030666280 scopus 로고    scopus 로고
    • Uneyama et al. recently demonstrated successful intramolecular radical cyclization of corresponding bisallyl α,α-difluoroamides: Uneyama, K.; Yanagiguchi, T.; Asai, H. Tetrahedron Lett. 1997, 38, 7763.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7763
    • Uneyama, K.1    Yanagiguchi, T.2    Asai, H.3
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    • note
    • MacSpartan Plus was employed for MO (PM3) calculation.
  • 79
    • 0345385669 scopus 로고    scopus 로고
    • note
    • #, -207.58 kcal/mol; S-trans-3b‡, -211.44 kcal/mol.
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    • 0000878597 scopus 로고
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    • Graham, S.M.1    Prestwich, G.D.2
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    • Graham, S. M.; Prestwich, G. D. J. Org. Chem. 1994, 59, 2956. Duran, I.; Parilla, A.; Feixas, J.; Guerrero, A. Bioorg. Med. Chem. Lett. 1993, 3, 2953. Rosell, G.; Herrero, S.; Guerrero, A. Biochem. Biophys. Res. Commun. 1996, 226, 227.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.