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Volumn 124, Issue 39, 2002, Pages 11689-11698

Asymmetric carbon-carbon bond formations in conjugate additions of lithiated N-Boc allylic and benzylic amines to nitroalkenes: Enantioselective synthesis of substituted piperidines, pyrrolidines, and pyrimidinones

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS;

EID: 0037009997     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0271375     Document Type: Article
Times cited : (102)

References (38)
  • 9
    • 0036089366 scopus 로고    scopus 로고
    • (a) For a review of asymmetric conjugate additions to nitroalkenes, see: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877. (b) Mulzer, J.; Zuhse, R.; Schmiechen, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 870. (c) Brenner, M.; Seebach, D. Helv. Chim. Acta 1999, 82, 2365. (d) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenburger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215.
    • (2002) Eur. J. Org. Chem. , pp. 1877
    • Berner, O.M.1    Tedeschi, L.2    Enders, D.3
  • 10
    • 33748223520 scopus 로고
    • (a) For a review of asymmetric conjugate additions to nitroalkenes, see: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877. (b) Mulzer, J.; Zuhse, R.; Schmiechen, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 870. (c) Brenner, M.; Seebach, D. Helv. Chim. Acta 1999, 82, 2365. (d) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenburger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 870
    • Mulzer, J.1    Zuhse, R.2    Schmiechen, R.3
  • 11
    • 0033452058 scopus 로고    scopus 로고
    • (a) For a review of asymmetric conjugate additions to nitroalkenes, see: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877. (b) Mulzer, J.; Zuhse, R.; Schmiechen, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 870. (c) Brenner, M.; Seebach, D. Helv. Chim. Acta 1999, 82, 2365. (d) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenburger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 2365
    • Brenner, M.1    Seebach, D.2
  • 12
    • 0033520797 scopus 로고    scopus 로고
    • (a) For a review of asymmetric conjugate additions to nitroalkenes, see: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877. (b) Mulzer, J.; Zuhse, R.; Schmiechen, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 870. (c) Brenner, M.; Seebach, D. Helv. Chim. Acta 1999, 82, 2365. (d) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenburger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10215
    • Ji, J.1    Barnes, D.M.2    Zhang, J.3    King, S.A.4    Wittenburger, S.J.5    Morton, H.E.6
  • 14
    • 0028796211 scopus 로고
    • For syntheses of enantioenriched substituted pyrimidinones see: Chan, A. W.-Y.; Ganem, B. Tetrahedron Lett. 1995, 36, 811.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 811
    • Chan, A.W.-Y.1    Ganem, B.2
  • 17
    • 2142683179 scopus 로고    scopus 로고
    • Provided in Supporting Information
    • Provided in Supporting Information.
  • 18
    • 2142790666 scopus 로고    scopus 로고
    • note
    • Crystallographic data for compounds have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. 190127-190133. These data can be obtained free of charge via www.c-cdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: +44 1223 336033; e-mail: deposit@ ccdc@cam.ac.uk)
  • 23
    • 2142779235 scopus 로고    scopus 로고
    • note
    • 1,3 strain in the equatorially lithiated intermediate, resulting in 93 being more reactive toward equatorial lithiation.
  • 30
    • 2142786871 scopus 로고    scopus 로고
    • note
    • The erosion of the enantiomeric ratio of ent-17 may indicate the transmetalation of 114 and 115 is not completely stereoselective.
  • 31


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