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Volumn 5, Issue 8, 2003, Pages 1341-1344

N-silyl-tethered radical cyclizations: A new synthesis of γ-amino alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; ALLYLAMINE; AMINOALCOHOL; ORGANOSILICON DERIVATIVE; PYRROLIDINE DERIVATIVE;

EID: 0037925366     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034288j     Document Type: Article
Times cited : (17)

References (32)
  • 1
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    • For the conceptualization of this, see: Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087-1088.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1087-1088
    • Stork, G.1    Kim, G.2
  • 7
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    • and references therein
    • (b) Ward, D. E.; Saeed Abaee, M. Org. Lett. 2000, 2, 3937-3940 and references therein.
    • (2000) Org. Lett. , vol.2 , pp. 3937-3940
    • Ward, D.E.1    Saeed Abaee, M.2
  • 8
    • 0001566548 scopus 로고
    • For reviews, see: (a) Bols, M.; Skydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (c) Gauthier, D.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338.
    • (1995) Chem. Rev. , vol.95 , pp. 1253-1277
    • Bols, M.1    Skydstrup, T.2
  • 9
    • 0030772750 scopus 로고    scopus 로고
    • For reviews, see: (a) Bols, M.; Skydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (c) Gauthier, D.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338.
    • (1997) Synthesis , pp. 813-854
    • Fensterbank, L.1    Malacria, M.2    Sieburth, S.M.3
  • 10
    • 0032510338 scopus 로고    scopus 로고
    • For reviews, see: (a) Bols, M.; Skydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (c) Gauthier, D.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338.
    • (1998) Tetrahedron , vol.54 , pp. 2289-2338
    • Gauthier, D.1    Zandi, K.S.2    Shea, K.J.3
  • 11
    • 0035969609 scopus 로고    scopus 로고
    • and references therein
    • For an exemple based on phosphonamide species, see: Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Org. Lett. 2001, 3, 3939-3942 and references therein.
    • (2001) Org. Lett. , vol.3 , pp. 3939-3942
    • Sprott, K.T.1    McReynolds, M.D.2    Hanson, P.R.3
  • 22
    • 0002148216 scopus 로고
    • Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York
    • Si-N bond is 77 kcal/mol, about 24 kcal/mol weaker than the Si-O bond. For a discussion of this, see: Armitage, D. A. In The Chemistry of the Silicon-Heteroatom Bond; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1991; pp 365-445.
    • (1991) The Chemistry of the Silicon-Heteroatom Bond , pp. 365-445
    • Armitage, D.A.1
  • 23
    • 24444465474 scopus 로고
    • Survey of literature data shows that only very few of these substrates with no functionality have been described; see: (a) Niederprüm, H.; Simmler, W. Chem. Ber. 1963, 96, 965-975. (b) Yoder, C. H.; Cader, B. M. J. Organomet. Chem. 1982, 233, 275-279 and references therein.
    • (1963) Chem. Ber. , vol.96 , pp. 965-975
    • Niederprüm, H.1    Simmler, W.2
  • 24
    • 0141659654 scopus 로고
    • and references therein
    • Survey of literature data shows that only very few of these substrates with no functionality have been described; see: (a) Niederprüm, H.; Simmler, W. Chem. Ber. 1963, 96, 965-975. (b) Yoder, C. H.; Cader, B. M. J. Organomet. Chem. 1982, 233, 275-279 and references therein.
    • (1982) J. Organomet. Chem. , vol.233 , pp. 275-279
    • Yoder, C.H.1    Cader, B.M.2
  • 25
    • 0000817704 scopus 로고
    • See also refs 15 and 16a
    • For a discussion of the cleavage of aminosilanes with ammonium salts, see: Anderson, H. H. J. Am. Chem. Soc. 1951, 73, 5802-5803. See also refs 15 and 16a.
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 5802-5803
    • Anderson, H.H.1
  • 29
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    • Compound 2e has been prepared by two consecutive N-silylations of allylamine (72% yield) and been found to be stable to aqueous workup and bulb to bulb distillation. For a rationalization of this stability, see: Schorr, M.; Schmitt, W. Phosphorus, Sulfur, Silicon 1992, 68, 25-35.
    • (1992) Phosphorus, Sulfur, Silicon , vol.68 , pp. 25-35
    • Schorr, M.1    Schmitt, W.2
  • 31
    • 0001557323 scopus 로고
    • For a model of the reduction of vinyl radicals, see: Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085-3093.
    • (1992) J. Org. Chem. , vol.57 , pp. 3085-3093
    • Journet, M.1    Malacria, M.2


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