메뉴 건너뛰기




Volumn 69, Issue 22, 2004, Pages 7705-7709

New synthetic approach to cyclopenta-fused heterocycles based upon a mild nazarov reaction. 2. Further studies on the torquoselectivity

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; DERIVATIVES; PALLADIUM; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 6344243267     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0489263     Document Type: Article
Times cited : (50)

References (47)
  • 4
    • 0000646877 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 751-784.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 751-784
    • Denmark, S.E.1
  • 11
    • 33845554840 scopus 로고
    • For processes involving β-silyl- or β-stannyl-substituted dienones, see: (a) Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642-2645.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 2642-2645
    • Denmark, S.E.1    Jones, T.K.2
  • 26
    • 17744417463 scopus 로고    scopus 로고
    • For a review on the chemistry and biology of roseophilin, see: Fürstner A. Angew. Chem., Int. Ed. 2003, 42, 3582-3603.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3582-3603
    • Fürstner, A.1
  • 27
    • 1642277252 scopus 로고    scopus 로고
    • and references therein
    • Nomura, I.; Mukai, C. J. Org. Chem. 2004, 69, 1803-1812 and references therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 1803-1812
    • Nomura, I.1    Mukai, C.2
  • 30
    • 0037587486 scopus 로고    scopus 로고
    • and references therein
    • Leclerc, E.; Tius, M. A. Org. Lett. 2003, 5, 1171-1174 and references therein.
    • (2003) Org. Lett. , vol.5 , pp. 1171-1174
    • Leclerc, E.1    Tius, M.A.2
  • 34
    • 2942555626 scopus 로고    scopus 로고
    • For a recent review on the chemistry of lactam-derived vinyl inflates, see: Occhiato, E. G. Mini-Rev. Org. Chem. 2004, 1, 149-162.
    • (2004) Mini-Rev. Org. Chem. , vol.1 , pp. 149-162
    • Occhiato, E.G.1
  • 37
    • 0030878188 scopus 로고    scopus 로고
    • In other cases we prepared, and successfully used in coupling reactions, the lactone-derived vinyl phosphates; see ref 9a. For the use of lactone-derived vinyl phosphates in Pd-catalyzed coupling reactions, see: Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gartner, P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467-5468.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5467-5468
    • Nicolaou, K.C.1    Shi, G.-Q.2    Gunzner, J.L.3    Gartner, P.4    Yang, Z.5
  • 38
    • 6344238142 scopus 로고    scopus 로고
    • note
    • 3 and in the presence of Amberlyst 15 afford the separable mixture of divinyl ketone 16 and cyclopenta-fused heterocycle 17 in a ratio strongly depending on the amount of water (or protic solvents such as alcohols) present in the solvent. For example, the hydrolysis of 15a with Amberlyst 15 in commercial chloroform afforded dienone 16a in 18% yield (see the Experimental Section).
  • 39
    • 84986437005 scopus 로고
    • MacroModel-An integrated software system for modeling organic and bioorganic molecules using molecular mechanics
    • The MM2* force field was used for the energy minimization with MacroModel software. Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel-An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467.
    • (1990) J. Comput. Chem. , vol.11 , pp. 440-467
    • Mohamadi, F.1    Richards, N.G.2    Guida, W.C.3    Liskamp, R.4    Lipton, M.5    Caufield, C.6    Chang, G.7    Hendrickson, T.8
  • 40
    • 6344288301 scopus 로고    scopus 로고
    • note
    • We thank one of the reviewers for the suggestion regarding the possible mechanism of cyclization that leads to the spiro compounds.
  • 41
    • 6344270991 scopus 로고    scopus 로고
    • note
    • In our earlier paper (see ref 9a), we assumed that a transition structure in which the heterocycle had a chairlike conformation could be favored.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.