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Volumn , Issue 8, 2000, Pages 1595-1601

Oxazoline N-oxide mediated [3+2] cycloadditions: Application to a formal synthesis of a (+)-β-methylcarbapenem

Author keywords

Blaise reaction; Cycloadditions; Lactams; Oxazoline N oxide; Thienamycin

Indexed keywords

BETA LACTAM DERIVATIVE; CARBAPENEM DERIVATIVE;

EID: 0034099893     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200004)2000:8<1595::aid-ejoc1595>3.3.co;2-5     Document Type: Article
Times cited : (15)

References (33)
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    • [1a] For a recent application to β-lactone synthesis, see: O. Dirat, C. Kouklovsky, Y. Langlois, J. Org. Chem. 1998, 63, 6634-6642 and references therein.
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    • Dirat, O.1    Kouklovsky, C.2    Langlois, Y.3
  • 2
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    • [1b] For a review on oxazoline N-oxides [2 + 3] cycloadditions, see: Y. Langlois, Curr. Org. Chem. 1998, 2, 1-18.
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  • 3
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    • [1c] For a review on asymmetric 1,3-dipolar cycloadditions, see: K. V. Gothelf, K. A. Jorgensen, Chem. Rev. 1998, 98, 863-909.
    • (1998) Chem. Rev. , vol.98 , pp. 863-909
    • Gothelf, K.V.1    Jorgensen, K.A.2
  • 8
    • 85083140092 scopus 로고    scopus 로고
    • note
    • The corresponding exo adduct has been isolated in 10% yield after chromatographic purification. NOE experiments allowed an unambiguous determination of the two asymmetric centres in both endo and exo adducts.
  • 9
    • 0031794248 scopus 로고    scopus 로고
    • and references therein
    • For a recent preparation of enamino esters, see: [6a] S. Fustero, M. G. de la Torre, V. Jofré, R. Pérez Carlon, A. Navarro, A. S. Fuentes, J. Org. Chem. 1998, 63, 8825-8836 and references therein. [6b] S. Fustero, M. D. Diaz, A. Navarro, E. Salavert, E. Aguilar. Tetrahedron Lett. 1999, 40, 1005-1008.
    • (1998) J. Org. Chem. , vol.63 , pp. 8825-8836
    • Fustero, S.1    De La Torre, M.G.2    Jofré, V.3    Pérez Carlon, R.4    Navarro, A.5    Fuentes, A.S.6
  • 10
    • 0033613777 scopus 로고    scopus 로고
    • For a recent preparation of enamino esters, see: [6a] S. Fustero, M. G. de la Torre, V. Jofré, R. Pérez Carlon, A. Navarro, A. S. Fuentes, J. Org. Chem. 1998, 63, 8825-8836 and references therein. [6b] S. Fustero, M. D. Diaz, A. Navarro, E. Salavert, E. Aguilar. Tetrahedron Lett. 1999, 40, 1005-1008.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1005-1008
    • Fustero, S.1    Diaz, M.D.2    Navarro, A.3    Salavert, E.4    Aguilar, E.5
  • 11
    • 0001688963 scopus 로고
    • Blaise reaction: [7a] E. E. Blaise, C. R. Acad. Sci. 1901, 132, 478-480 and 978-980.
    • (1901) C. R. Acad. Sci. , vol.132 , pp. 478-480
    • Blaise, E.E.1
  • 17
    • 85088332575 scopus 로고    scopus 로고
    • note
    • [1]). A possible protonation of dipolarophile 11 can enhance the reactivity of this compound in a [3 + 2] cycloaddition. This point is still under investigation.
  • 19
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    • [9b] For a review concerning the use of sodium cyanoborohydride, see: C. F. Lane, Synthesis 1975, 135-146.
    • (1975) Synthesis , pp. 135-146
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  • 20
    • 85083138240 scopus 로고    scopus 로고
    • Configurations of the side chain in 12 were confirmed after further transformation into β-lactam 18
    • Configurations of the side chain in 12 were confirmed after further transformation into β-lactam 18.
  • 21
    • 85083126987 scopus 로고    scopus 로고
    • note
    • The selectivity of this reduction step is highly dependant on both temperature and solvents: at 0°C or in methanol a mixture of four isomers was obtained. A better selectivity was observed in the thienamycin series, vide infra.
  • 23
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    • Ketol 15, isolated in 75% yield, can be transformed into hydroxylamino isoborneol and reused, see: T. Berranger, Y. Langlois, J. Org. Chem. 1995, 60, 1720-1726.
    • (1995) J. Org. Chem. , vol.60 , pp. 1720-1726
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  • 25
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    • For a review concerning the stereoselective preparation of β-amino acids, see: D. C. Dole, Tetrahedron 1994, 50, 9517-9582.
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Dole, D.C.1
  • 26
    • 85083147613 scopus 로고    scopus 로고
    • note
    • The value of the coupling constant C3H-C4H (J = 2.2 Hz) is characteristic for a trans relationship between these two hydrogens.
  • 28
    • 85088332722 scopus 로고    scopus 로고
    • note
    • 3).
  • 29
    • 85088332260 scopus 로고    scopus 로고
    • note
    • 3.
  • 30
    • 85083138464 scopus 로고    scopus 로고
    • note
    • With a cycloadduct substituted by a gem dimethyl group at C2, the diastereomer corresponding to compound 22b is the only product of the reaction. This result is also in agreement with a conformational restriction of the side chain due to hydrogen bonding in the iminium intermediate and a diastereoselective attack of hydride at the Re face of this iminium (unpublished work).


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