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Volumn 68, Issue 8, 2003, Pages 3271-3280

Selective ring contraction of 5-spirocyclopropane isoxazolidines mediated by acids

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ETHYLENE; EXTRUSION; POSITIVE IONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

EID: 0037453665     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034003g     Document Type: Article
Times cited : (41)

References (29)
  • 19
    • 0001728892 scopus 로고
    • Seebach, D. Angew. Chem. 1979, 91, 259-278; Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
    • (1979) Angew. Chem. , vol.91 , pp. 259-278
    • Seebach, D.1
  • 20
    • 0018454939 scopus 로고
    • Seebach, D. Angew. Chem. 1979, 91, 259-278; Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
    • (1979) Angew. Chem., Int. Ed. Engl. , vol.18 , pp. 239
  • 22
    • 0345635632 scopus 로고    scopus 로고
    • note
    • 3CN, reflux temperature, 15 min).
  • 23
    • 0345635633 scopus 로고    scopus 로고
    • note
    • 3NHOH and following the same procedure used for the synthesis of 38b.
  • 24
    • 33947471447 scopus 로고
    • This hypothesis recalls the first step of the Hoffman Loffler Freitag reaction that is the thermal induced homolysis of N-X bond in the presence of strong protic acid, where X is a chlorine or bromine atom: (a) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1668. (b) Wolff, M. E. Chem. Rev. 1963, 63, 55-64. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 1657-1668
    • Corey, E.J.1    Hertler, W.R.2
  • 25
    • 0002603882 scopus 로고
    • This hypothesis recalls the first step of the Hoffman Loffler Freitag reaction that is the thermal induced homolysis of N-X bond in the presence of strong protic acid, where X is a chlorine or bromine atom: (a) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1668. (b) Wolff, M. E. Chem. Rev. 1963, 63, 55-64. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350.
    • (1963) Chem. Rev. , vol.63 , pp. 55-64
    • Wolff, M.E.1
  • 26
    • 84985635446 scopus 로고
    • This hypothesis recalls the first step of the Hoffman Loffler Freitag reaction that is the thermal induced homolysis of N-X bond in the presence of strong protic acid, where X is a chlorine or bromine atom: (a) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1668. (b) Wolff, M. E. Chem. Rev. 1963, 63, 55-64. (c) Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337-350.
    • (1983) Angew. Chem., Int. Ed. Engl. , vol.22 , pp. 337-350
    • Stella, L.1
  • 28
    • 0344773088 scopus 로고    scopus 로고
    • note
    • The diastereomeric mixture of 5-spirocyclopropane isoxazolidines 71 was converted into the cis- and trans-quinolizidinones 76 in 28% and 52% isolated yield, respectively, by heating at 110 °C under neutral conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.