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Volumn 68, Issue 4, 2003, Pages 1394-1400

Michael addition of chloroalkyloxazolines to electron-poor alkenes: Synthesis of heterosubstituted cyclopropanes

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[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 0037458960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026661r     Document Type: Article
Times cited : (23)

References (36)
  • 12
    • 0004258370 scopus 로고
    • Patai, S., Rappoport, Z., Eds.; Wiley: New York
    • For examples of well-known cyclopropyl derivatives, see: Lin, H. W.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1987; Vol. 16. Martel, J. In Chirality in Industry; Collins, A. N., Sheldrake, N. G., Crosby, J., Eds.; Wiley: Chichester, U.K., 1992; Chapter 4 and references therein. Barrett, A. G. M.; Kasdorf, J. J. Am. Chem. Soc. 1996, 118, 11030-11037 and references therein. Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328 and references therein.
    • (1987) The Chemistry of the Cyclopropyl Group , vol.16
    • Lin, H.W.1    Walsh, C.T.2
  • 13
    • 0242666162 scopus 로고
    • Collins, A. N., Sheldrake, N. G., Crosby, J., Eds.; Wiley: Chichester, U.K.; Chapter 4 and references therein
    • For examples of well-known cyclopropyl derivatives, see: Lin, H. W.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1987; Vol. 16. Martel, J. In Chirality in Industry; Collins, A. N., Sheldrake, N. G., Crosby, J., Eds.; Wiley: Chichester, U.K., 1992; Chapter 4 and references therein. Barrett, A. G. M.; Kasdorf, J. J. Am. Chem. Soc. 1996, 118, 11030-11037 and references therein. Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328 and references therein.
    • (1992) Chirality in Industry
    • Martel, J.1
  • 14
    • 0029909231 scopus 로고    scopus 로고
    • and references therein
    • For examples of well-known cyclopropyl derivatives, see: Lin, H. W.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1987; Vol. 16. Martel, J. In Chirality in Industry; Collins, A. N., Sheldrake, N. G., Crosby, J., Eds.; Wiley: Chichester, U.K., 1992; Chapter 4 and references therein. Barrett, A. G. M.; Kasdorf, J. J. Am. Chem. Soc. 1996, 118, 11030-11037 and references therein. Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328 and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11030-11037
    • Barrett, A.G.M.1    Kasdorf, J.2
  • 15
    • 0029855416 scopus 로고    scopus 로고
    • and references therein
    • For examples of well-known cyclopropyl derivatives, see: Lin, H. W.; Walsh, C. T. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1987; Vol. 16. Martel, J. In Chirality in Industry; Collins, A. N., Sheldrake, N. G., Crosby, J., Eds.; Wiley: Chichester, U.K., 1992; Chapter 4 and references therein. Barrett, A. G. M.; Kasdorf, J. J. Am. Chem. Soc. 1996, 118, 11030-11037 and references therein. Charette, A. B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327-10328 and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10327-10328
    • Charette, A.B.1    Lebel, H.2
  • 16
    • 0242666163 scopus 로고    scopus 로고
    • Chapter 16.1, Lydon, K. M., McKervey, M. A., Eds.; Chapter 16.2, Charette, A. B., Lebel, H., Eds.; Chapter 16.3, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heildelberg, New York
    • For examples of direct carbene insertion into olefins from diazo precursors utilizing transition metals (stoichiometric and catalytic), see: Pfaltz, A. In Comprehensive Asymmetric Catalysis I-III; Chapter 16.1, Lydon, K. M., McKervey, M. A., Eds.; Chapter 16.2, Charette, A. B., Lebel, H., Eds.; Chapter 16.3, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heildelberg, New York, 2000.
    • (2000) Comprehensive Asymmetric Catalysis I-III
    • Pfaltz, A.1
  • 17
    • 2142690327 scopus 로고
    • For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
    • (1989) Chem. Rev. , vol.89 , pp. 1247-1270
    • Salaun, J.1
  • 18
    • 0001485086 scopus 로고    scopus 로고
    • and references therein
    • For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
    • (1997) Chem. Rev. , vol.97 , pp. 2341-2372
    • Li, A.-H.1    Dai, L.-X.2    Aggarwal, V.K.3
  • 19
    • 0032510368 scopus 로고    scopus 로고
    • For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1437-1440
    • Krief, A.1    Provins, L.2    Froidbise, A.3
  • 20
    • 0034836080 scopus 로고    scopus 로고
    • For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2964-2969
    • Taylor, R.E.1    Engelhardt, F.C.2    Schmitt, M.J.3    Yuan, H.4
  • 21
    • 0033828728 scopus 로고    scopus 로고
    • For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
    • (2000) J. Org. Chem. , vol.65 , pp. 5531-5546
    • Avery, T.D.1    Taylor, D.K.2    Tiekink, E.R.T.3
  • 22
    • 0035977249 scopus 로고    scopus 로고
    • For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
    • (2001) J. Org. Chem. , vol.66 , pp. 7955-7966
    • Avery, T.D.1    Fallon, G.2    Greatrex, B.W.3    Pyke, S.M.4    Taylor, D.K.5    Tiekink, E.R.T.6
  • 23
    • 0037012830 scopus 로고    scopus 로고
    • and references therein
    • For examples of Michael addition of nucleophiles to α,β-unsaturated ketones and esters followed by intramolecular cyclization, see: Salaun, J. Chem. Rev. 1989, 89, 1247-1270. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372 and references therein. Krief, A.; Provins, L.; Froidbise, A. Tetrahedron Lett. 1998, 39, 1437-1440. For synthesis via cationic intermediates, see: Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964-2969. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966. Kimber, M. C.; Taylor, D. K. J. Org. Chem. 2002, 67, 3142-3144 and references therein.
    • (2002) J. Org. Chem. , vol.67 , pp. 3142-3144
    • Kimber, M.C.1    Taylor, D.K.2
  • 25
    • 0035296971 scopus 로고    scopus 로고
    • 13C-deshielding (Δδ = 12.73 ppm). This result could be accounted for in terms of a low carbenoid character (Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756) associated with the above-mentioned Li/Cl carbenoid species (in contrast to a higher one found in the case of the 2-chloromethyl-2-oxazoline; see ref 1) that would justify its greater thermodynamic stability and a less pronounced tendency toward an "eliminative dimerization" process so typical of carbenoid species.
    • (2001) Chem. Rev. , vol.101 , pp. 697-756
    • Boche, G.1    Lohrenz, J.C.W.2
  • 26
    • 0002649043 scopus 로고
    • Kagan, H. B., Ed.; George Thieme Publishers, Stuttgart, Determination of configurations by spectrometric methods
    • Gaudemar, A. In Stereochemistry: fundamentals and methods; Kagan, H. B., Ed.; George Thieme Publishers: Stuttgart, 1977; Vol. 1, Determination of configurations by spectrometric methods, pp 77-83.
    • (1977) Stereochemistry: Fundamentals and Methods , vol.1 , pp. 77-83
    • Gaudemar, A.1
  • 28
    • 0242497686 scopus 로고    scopus 로고
    • note
    • NOESY phase-sensitive experiments performed on compounds 8, 12a, and 13a also showed that, as a general pattern, the most deshielded cyclopropane ring hydrogen was always the one between the two heterocyclic rings, and that an oxazoline ring had, on the other hydrogen, a greater shielding effect with respect to a phenyl-substituted ring.
  • 34
    • 85056022271 scopus 로고    scopus 로고
    • note
    • 3)} was prepared as reported in the case of 20a (see ref 4d).


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