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Volumn 1997, Issue 2, 1997, Pages 179-180

A New Method to Generate α-Aminoalkyl Radicals: Treatment of Methyl α-Amino Selenoesters with Hydride Reagents. Synthesis of 6-Azabicyclo[3.2.1]octanes by Radical Cyclization

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EID: 0002639377     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-724     Document Type: Article
Times cited : (30)

References (36)
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    • For a review on 1-amino- and 1-amidoalkyl radicals, see: Renaud, P.; Giraud, L. Synthesis 1996, 913.
    • (1996) Synthesis , pp. 913
    • Renaud, P.1    Giraud, L.2
  • 5
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    • (b) Curran, D. P.; Sun, S. Tetrahedron Lett. 1993, 34, 6181. See also: Della, E. W.; Knill, A. M.; Smith, P. A. Chem. Commun. 1996, 1637.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6181
    • Curran, D.P.1    Sun, S.2
  • 12
    • 0000392488 scopus 로고    scopus 로고
    • For recent syntheses, see: (a) Rigby, J. H.; Pigge, F. C. Synlett 1996, 631. (b) Callis, D. J.; Thomas, N. F.; Pearson, D. P. J.; Potter, B. V. L. J. Org. Chem. 1996, 61, 4634.
    • (1996) Synlett , pp. 631
    • Rigby, J.H.1    Pigge, F.C.2
  • 14
    • 0019140070 scopus 로고
    • For decarbonylation processes of acyl radicals generated starting from phenyl selenoesters, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
    • (1980) Helv. Chim. Acta , vol.63 , pp. 2328
    • Pfenninger, J.1    Heuberger, C.2    Graf, W.3
  • 15
    • 0022006648 scopus 로고
    • For decarbonylation processes of acyl radicals generated starting from phenyl selenoesters, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3285
    • Ireland, R.E.1    Norbeck, D.W.2    Mandel, G.S.3    Mandel, N.S.4
  • 16
    • 1542586402 scopus 로고
    • For decarbonylation processes of acyl radicals generated starting from phenyl selenoesters, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (c) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429.
    • (1992) J. Org. Chem. , vol.57 , pp. 1429
    • Boger, D.L.1    Mathvink, R.J.2
  • 18
    • 0003067028 scopus 로고    scopus 로고
    • (c) The synthetic application of this decarbonylation-type is documented: Stojanovic, A.; Renaud, P. Synlett, 1997, 181.
    • (1997) Synlett , pp. 181
    • Stojanovic, A.1    Renaud, P.2
  • 20
    • 1542655041 scopus 로고    scopus 로고
    • note
    • 12 but to our knowledge there are no precedents for this transformation from α-dialkylamino acid derivatives via a radical procedure.
  • 25
    • 1542760266 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra, as well as appropriate parent ion identification by HRMS. In addition, compounds 2-4, 8, and 12 gave satisfactory combustion analyses.
  • 27
  • 30
    • 1542550064 scopus 로고    scopus 로고
    • note
    • 2Ar), 122.3(CN), 126.8, 128.1, 128.2, 140.0 (Ar).
  • 32
    • 1542655046 scopus 로고    scopus 로고
    • note
    • 2Ar), 122.3 (CN), 127.0, 127.8, 128.6, and 139.0(Ar), 206.7 (C-5).
  • 36
    • 0027953358 scopus 로고
    • For the synthesis of bridged azabicyclic compounds using aminyl radicals, see: Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron 1994, 50, 1295.
    • (1994) Tetrahedron , vol.50 , pp. 1295
    • Bowman, W.R.1    Clark, D.N.2    Marmon, R.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.