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Volumn 127, Issue 27, 2005, Pages 9708-9709

Gold(I)-catalyzed ring expansion of cyclopropanols and cyclobutanols

Author keywords

[No Author keywords available]

Indexed keywords

BUTANOL; CYCLOBUTANOL; CYCLOPROPANOL; GOLD; PROPANOL; UNCLASSIFIED DRUG;

EID: 22144454984     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052831g     Document Type: Article
Times cited : (198)

References (33)
  • 1
    • 0001373505 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: London
    • (a) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: London, 1991; Vol. 5; p 899.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 899
    • Hudlicky, T.1    Reed, J.W.2
  • 4
    • 0034830059 scopus 로고    scopus 로고
    • For an enantio-selective rearrangement of vinylcycloalkanols, see: (d) Trost, B. M.; Yasukata, T. J. Am. Chem. Soc. 2001, 123, 7162.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7162
    • Trost, B.M.1    Yasukata, T.2
  • 8
    • 32744468380 scopus 로고    scopus 로고
    • note
    • Co(0)-catalyzed expansion of 1-alkynylcyclopropanols affords cyclopentenones and, in some cases, small amounts of the alkylidenecyclobutanone:
  • 22
    • 8744259772 scopus 로고    scopus 로고
    • For an excellent review of homogeneous gold-catalyzed reactions, see: Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
    • (2004) Gold Bull. , vol.37 , pp. 51
    • Hashmi, A.S.K.1
  • 23
    • 32744455305 scopus 로고
    • For reviews of Ag(I)-catalyzed rearrangement of strained oσ-bonds, see: (a) Paquette, L. A. Acc. Chem. Res. 1971, 4, 281.
    • (1971) Acc. Chem. Res. , vol.4 , pp. 281
    • Paquette, L.A.1
  • 24
    • 0009679346 scopus 로고
    • (b) Bishop, K. C., III. Chem. Rev. 1976, 76, 461. For Au-catalyzed rearrangement of small ring hydrocarbons, see:
    • (1976) Chem. Rev. , vol.76 , pp. 461
    • Bishop III, K.C.1
  • 27
    • 32744454922 scopus 로고    scopus 로고
    • note
    • Under identical reaction conditions. Au(I)-catalyzed reaction of non-terminal alkynylcyclobutanols produced complex mixtures.
  • 28
    • 22144432396 scopus 로고
    • For stoichioraetric formation of triphenylphosphinegold(I)-homoenolates from cyclopropanols, see: Murakami, M.; Inouve, M.; Suginome, M.; Ito, Y. Bull. Chem. Soc. Jpn. 1988, 61, 3649. In accord with this report, we found that 3 catalyzed the rearrangement of vinylcyclopropanol 42 to ketone 43. (Diagram presented)
    • (1988) Bull. Chem. Soc. Jpn. , vol.61 , pp. 3649
    • Murakami, M.1    Inouve, M.2    Suginome, M.3    Ito, Y.4
  • 29
    • 0033599513 scopus 로고    scopus 로고
    • A related mechanism has been proposed for formation of methylidene cyclopentanones by Pd(II)-catalyzed rearrangement of a vinylcyclobutanols. See: Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2645
    • Nishimura, T.1    Ohe, K.2    Uemura, S.3
  • 30
    • 32744457556 scopus 로고    scopus 로고
    • note
    • Consistent with the kinetic formation of (E)-alkenes, olefin geometry in cyclobutanone 44 is not isomerized under the reaction conditions. (Diagram presented)
  • 31
    • 32744471239 scopus 로고
    • For an example of reversal of migratory aptitude in ring expansion due to inductive effects, see: Trost, B. M.; Ornstein, P. L. J. Ori>. Chem. 1985, 48, 1133.
    • (1985) J. Ori>. Chem. , vol.48 , pp. 1133
    • Trost, B.M.1    Ornstein, P.L.2
  • 32
    • 20344385562 scopus 로고    scopus 로고
    • For recent approaches to highly substituted cyclopentanones from vinyl cyclopropanes, see: (a) Navseschuk, C. G.; Rovis, T. Angew. Chem., Int. Ed. 2005, 44, 3264.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3264
    • Navseschuk, C.G.1    Rovis, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.