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Volumn 71, Issue 24, 2006, Pages 9144-9152

Stereocontrolled synthesis of functionalized cis-cyclopentapyrazolidines by 1,3-dipolar cycloaddition reactions of azomethine imines

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ESTERS; NITROGEN COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 33751560221     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061537j     Document Type: Article
Times cited : (47)

References (52)
  • 1
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    • Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products
    • Padwa, A., Pearson, W. H., Eds.; Wiley: Chichester
    • Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Chemistry of Heterocyclic Compounds Series 59; Wiley: Chichester, 2002.
    • (2002) Chemistry of Heterocyclic Compounds Series 59
  • 4
    • 33645410218 scopus 로고    scopus 로고
    • Azomethine Imines
    • Georg Thieme Verlag: Stuttgart
    • (a) Schantl, J. G. Azomethine Imines. Science of Synthesis; Georg Thieme Verlag: Stuttgart, 2004; Vol. 27, pp 731-824.
    • (2004) Science of Synthesis , vol.27 , pp. 731-824
    • Schantl, J.G.1
  • 5
    • 0000629986 scopus 로고
    • Intermolecular 1.3-Dipolar Cycloadditions
    • Trost, B. M., Fleming, I., Eds.; Pergamon; London
    • (b) Padwa, A. Intermolecular 1.3-Dipolar Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon; London, 1991; Vol. 4, pp 1069-1109.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069-1109
    • Padwa, A.1
  • 6
    • 0000629986 scopus 로고
    • Intramolecular 1,3-Dipolar Cycloadditions: Azomethine Imine Cyclizations
    • Trost, B. M., Fleming, I., Eds.; Pergamon: London
    • (c) Wade, P. A. Intramolecular 1,3-Dipolar Cycloadditions: Azomethine Imine Cyclizations. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 4, pp 1144-49.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1144-1149
    • Wade, P.A.1
  • 25
    • 33751559949 scopus 로고    scopus 로고
    • note
    • Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614479.
  • 26
    • 33751559239 scopus 로고    scopus 로고
    • note
    • Other solvents examined: toluene, 1,2-dichloroethane, acetic acid, acetonitrile, 2,2,2-trifluoroethanol, and N,N-dimethylformamide.
  • 27
    • 33751583402 scopus 로고    scopus 로고
    • note
    • Wittig reaction of aldehyde 8 with methoxymethyltriphenylphosphonium chloride and potassium hexamethyldisilazane (KHMDS) in THF, followed by hydrolysis of the resulting enol ether with aqueous hydrochloric acid in THF, gave aldehyde 48 in 85% yield over two steps.
  • 28
    • 33751565051 scopus 로고    scopus 로고
    • note
    • A Monte Carlo conformational search was performed using the MMFF force field as implemented in Spartan 2005.
  • 29
    • 33751568183 scopus 로고    scopus 로고
    • note
    • The cis cycloadduct 41 was calculated to have a conformational energy of 163.4 kcal/mol, whereas the cycloadduct (epimeric at C3 and C3a) had a conformational energy of 171.9 kcal/mol.
  • 31
    • 33751564892 scopus 로고    scopus 로고
    • note
    • Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614481.
  • 32
    • 33751561986 scopus 로고    scopus 로고
    • note
    • Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614480.
  • 33
    • 33751559077 scopus 로고    scopus 로고
    • note
    • The toluene/PPTS conditions were also examined with substrates that contained α-methoxy, α,β-unsaturated esters dipolarophile fragments. In these cases, the cycloaddition substrates decomposed to give intractable mixtures.
  • 34
    • 33751560693 scopus 로고    scopus 로고
    • note
    • Crystallographic data for this compound were deposited at the Cambridge Crystallographic Data Centre: CCDC 614482.
  • 42
    • 0041931082 scopus 로고    scopus 로고
    • Lewis acids have also been used to promote related azomethine ylide cycloadditions: (a) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10174-10175
    • Chen, C.1    Li, X.2    Schreiber, S.L.3
  • 45
    • 33751570209 scopus 로고    scopus 로고
    • note
    • 2.
  • 46
    • 29244479725 scopus 로고    scopus 로고
    • For a general review of microwave chemistry, see: Galema, S. A. Chem. Soc. Rev. 1997, 26, 233-238.
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 233-238
    • Galema, S.A.1
  • 51
    • 0037377598 scopus 로고    scopus 로고
    • Although bicyclo[3.3.0]octane ring systems are generally observed in intermolecular dipolar cycloadditions in which a dipole is connected to an alkene through a three-carbon tether, bicyclo[3.2.1]octane ring systems have been observed, see: Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628.
    • (2003) Curr. Org. Chem. , vol.7 , pp. 585-628
    • Koumbis, A.E.1    Gallos, J.K.2
  • 52
    • 0035913709 scopus 로고    scopus 로고
    • All cycloaddition reactions were performed in thick-walled sealed tubes for reaction volumes greater than 2 mL and in screw-cap vials with Teflon caps for reaction volumes of 2 mL or less. Other general experimental details have been described: MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9033-9044
    • MacMillan, D.W.C.1    Overman, L.E.2    Pennington, L.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.