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Volumn 72, Issue 6, 2007, Pages 2127-2132

Stannane-free chemoselective hydrodehalogenation of 4-halotetrahydropyrans: Scope and application to natural product synthesis

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOSELECTIVITY; DEBENZYLATION; ENANTIOSELECTIVE SYNTHESIS; HYDRODEHALOGENATION;

EID: 33947193601     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0624871     Document Type: Article
Times cited : (6)

References (36)
  • 3
    • 85197362507 scopus 로고    scopus 로고
    • For recent references on biological evaluations of selected tetrahydropyran containing natural products, see: (a) Michelet, W, Genet, J. P. Curr. Org. Chem. 2005, 9, 405
    • For recent references on biological evaluations of selected tetrahydropyran containing natural products, see: (a) Michelet, W.; Genet, J. P. Curr. Org. Chem. 2005, 9, 405.
  • 6
    • 33947285155 scopus 로고    scopus 로고
    • Selected references on Prins cyclization: (a) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913.
    • Selected references on Prins cyclization: (a) Coppi, L.; Ricci, A.; Taddei, M. J. Org. Chem. 1988, 53, 913.
  • 15
    • 0000893313 scopus 로고    scopus 로고
    • Paquette, L, Beak, P, Engelbert, C, Curran, D, Czarnik, A, Scott, E, Hegedus, L, Kelly, R, Overman, L, Roush, W. R, Smith, A, White, J, Eds, Wiley & Sons: New York
    • (b) Glese, B.; Gobel, T.; Dickhaut, G.; Thoma, G.; Kulicke, K. J.; Trach, F. In Organic Reactions; Paquette, L., Beak, P., Engelbert, C., Curran, D., Czarnik, A., Scott, E., Hegedus, L., Kelly, R., Overman, L., Roush, W. R., Smith, A., White, J., Eds.; Wiley & Sons: New York, 1996; pp 301-856.
    • (1996) Organic Reactions , pp. 301-856
    • Glese, B.1    Gobel, T.2    Dickhaut, G.3    Thoma, G.4    Kulicke, K.J.5    Trach, F.6
  • 22
    • 33947263911 scopus 로고    scopus 로고
    • For the synthesis of 4-halo-2,6-disubstituted THP substrates, see: (a) Chan, K. P.; Loh, T. P. Tetrahedron. Lett. 2004, 45, 1167.
    • For the synthesis of 4-halo-2,6-disubstituted THP substrates, see: (a) Chan, K. P.; Loh, T. P. Tetrahedron. Lett. 2004, 45, 1167.
  • 29
    • 1542287662 scopus 로고    scopus 로고
    • For other syntheses of (+)-SCH 351448, see: (a) Kang, E. J.; Cho, E. J.; Lee, Y. E.; Ji, M. K.; Shin, D. M.; Chung, Y. K.; Lee, E. J. Am. Chem. Soc. 2004, 126, 2680.
    • For other syntheses of (+)-SCH 351448, see: (a) Kang, E. J.; Cho, E. J.; Lee, Y. E.; Ji, M. K.; Shin, D. M.; Chung, Y. K.; Lee, E. J. Am. Chem. Soc. 2004, 126, 2680.
  • 35
    • 33947196524 scopus 로고    scopus 로고
    • The reaction has been demonstrated to up to 30 mmol scale with the final product (8) yield of 66
    • The reaction has been demonstrated to up to 30 mmol scale with the final product (8) yield of 66%.
  • 36
    • 33947262238 scopus 로고    scopus 로고
    • ACCN denotes 1,1′,-azobis(cyclohexane)carbonitrile, a synthetic equivalent to AIBN.
    • ACCN denotes 1,1′,-azobis(cyclohexane)carbonitrile, a synthetic equivalent to AIBN.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.