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Volumn , Issue 7, 1999, Pages 1033-1036

Novel annelation methodology for the rapid and efficient construction of bicyclo [4.n.0] alkanols and alkenones

Author keywords

Annelation; Bicycles; Enones; Orthoesters; Silylenol ethers

Indexed keywords

ALKANOL; ALKANONE; BICYCLO COMPOUND; ETHER DERIVATIVE;

EID: 0032789966     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2768     Document Type: Article
Times cited : (15)

References (40)
  • 1
    • 0002292348 scopus 로고
    • See for example: (a) Jung, M.E. Tetrahedron 1976, 32, 3-31.
    • (1976) Tetrahedron , vol.32 , pp. 3-31
    • Jung, M.E.1
  • 19
    • 0000655751 scopus 로고
    • Trost, B.M.; Fleming, I. Eds,; Pergamon: Oxford
    • (d) Kantlehner, W. in Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I. Eds,; Pergamon: Oxford, 1991; Vol 6, p556-599.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 556-599
    • Kantlehner, W.1
  • 36
    • 0344550000 scopus 로고    scopus 로고
    • note
    • 2 required probably reflects the chelation of the lanthanide reagent by the dioxolane substituent.
  • 37
    • 0345412210 scopus 로고    scopus 로고
    • note
    • This selectivity could be attributed to the large steric bulk of the organosamarium reagent. See also references 9a-9c.
  • 38
    • 0344118338 scopus 로고    scopus 로고
    • note
    • In the case of the hydrindane derivative, the cis-ring junction is thermodynamically preferred.
  • 39
    • 0000257577 scopus 로고    scopus 로고
    • The stereochemistry of several bicyclic alcohols was unambiguously established by X-ray crystallographic analysis either of the ketal-containing bicycle (Table 2, Entry 4) or of the corresponding hydroxyketone obtained by CAN-catalysed deprotection (Table 2, Entries 2 and 5). The stereochemistry of the other bicyclic derivatives was established by spectroscopic correlation. Tinant, B.; Feneau-Dupont, J.; Declercq, J.-P.; Ates, A.; Markó, I.E. Bull. Soc. Chim. Belg. 1997, 106, 297.
    • (1997) Bull. Soc. Chim. Belg. , vol.106 , pp. 297
    • Tinant, B.1    Feneau-Dupont, J.2    Declercq, J.-P.3    Ates, A.4    Markó, I.E.5
  • 40
    • 0344980942 scopus 로고    scopus 로고
    • note
    • +, 62).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.