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Volumn , Issue 20, 2008, Pages 3091-3105

DBU-promoted elimination reactions of vicinal dibromoalkanes mediated by adjacent O-functional groups, and applications to the synthesis of biologically active natural products

Author keywords

Acidity enhancement; Alkynes; Bromoalkenes; Dibromoalkanes; Regioselective elimination

Indexed keywords


EID: 58149341772     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1087360     Document Type: Review
Times cited : (19)

References (125)
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    • 1H NMR integration.
    • 1H NMR integration.
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    • The 1,2-dibromoalkanes 1 were synthesized from the corresponding olefins. 1-O-Substituted 3-alkyl-2,3-dibromoalkanes 1f and 1g were synthesized by trans dibromination of the corresponding Z- and E-olefin, respectively. For the corresponding olefinic compounds 1a and 1b, see: (a) Vowinkel, E
    • The 1,2-dibromoalkanes 1 were synthesized from the corresponding olefins. 1-O-Substituted 3-alkyl-2,3-dibromoalkanes 1f and 1g were synthesized by trans dibromination of the corresponding Z- and E-olefin, respectively. For the corresponding olefinic compounds 1a and 1b, see: (a) Vowinkel, E. Chem. Ber. 1962, 95, 2997.
    • (1962) Chem. Ber , vol.95 , pp. 2997
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    • For 1c, see: (b) Sonnenberg, F. M. J. Org. Chem. 1970, 35, 3166.
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    • For 1d, 1q, 1t, 1v, 1w, 1x, and 1y, see ref. 13b. For 1e, 1h, 1k, 1l, 1m, 1n, 1p, and 1r, see ref. 36. For 1f and 1g, see: (c) Goux, C.; Massacret, M.; Lhoste, P.; Sinou, D. Organometallics 1995, 14, 4585.
    • For 1d, 1q, 1t, 1v, 1w, 1x, and 1y, see ref. 13b. For 1e, 1h, 1k, 1l, 1m, 1n, 1p, and 1r, see ref. 36. For 1f and 1g, see: (c) Goux, C.; Massacret, M.; Lhoste, P.; Sinou, D. Organometallics 1995, 14, 4585.
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    • For 1i, see: (d) Stefane, B.; Kocevar, M.; Polanc, S. Tetrahedron Lett. 1999, 40, 4429.
    • For 1i, see: (d) Stefane, B.; Kocevar, M.; Polanc, S. Tetrahedron Lett. 1999, 40, 4429.
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    • For 1j, see: (e) Hennion, G. F.; Barrett, S. O. J. Am. Chem. Soc. 1957, 79, 2146.
    • For 1j, see: (e) Hennion, G. F.; Barrett, S. O. J. Am. Chem. Soc. 1957, 79, 2146.
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    • For 1o, see ref. 34b. For 1s, see: (f) Yokoyama, T.; Ohgiya, T.; Nishiyama, S.; unpublished experiments; Keio University: Japan, 2006;
    • For 1o, see ref. 34b. For 1s, see: (f) Yokoyama, T.; Ohgiya, T.; Nishiyama, S.; unpublished experiments; Keio University: Japan, 2006;
  • 53
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    • For 1u, see: (g) White, W. N.; Gwynn, D.; Schlitt, R.; Girard, C.; Fife, W. J. Am. Chem. Soc. 1958, 80, 3271.
    • For 1u, see: (g) White, W. N.; Gwynn, D.; Schlitt, R.; Girard, C.; Fife, W. J. Am. Chem. Soc. 1958, 80, 3271.
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    • Finn, M. G.; Sharpless, K. B. On the Mechanism of Asymmetric Epoxidation with Titanium-Tartrate Catalysts, In Asymmetric Synthesis, 5; Morrison, J. D., Ed.; Academic Press: Tokyo, 1985, 247.
    • (a) Finn, M. G.; Sharpless, K. B. On the Mechanism of Asymmetric Epoxidation with Titanium-Tartrate Catalysts, In Asymmetric Synthesis, Vol. 5; Morrison, J. D., Ed.; Academic Press: Tokyo, 1985, 247.
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    • 1H NMR spectrum of the corresponding MTPA esters.
    • 1H NMR spectrum of the corresponding MTPA esters.
  • 94
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    • For examples of regioselective elimination from styrene dibromide with other bases, see: (a) Hehmlow, E. V, Schell, H. G. Chem. Ber. 1980, 113, 1
    • For examples of regioselective elimination from styrene dibromide with other bases, see: (a) Hehmlow, E. V.; Schell, H. G. Chem. Ber. 1980, 113, 1.
  • 98
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    • PhD Thesis; Keio University: Japan
    • Ohgiya, T. PhD Thesis; Keio University: Japan, 2005.
    • (2005)
    • Ohgiya, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.