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Volumn 125, Issue 8, 2003, Pages 2028-2029

Novel iminium ion equivalents prepared through C-H oxidation for the stereocontrolled synthesis of functionalized propargylic amine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; IMINE;

EID: 0037466996     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028916o     Document Type: Article
Times cited : (109)

References (26)
  • 1
    • 0035232404 scopus 로고    scopus 로고
    • Cordell, G. A., Ed.; Academic Press: San Diego
    • (a) Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; Vol. 55, pp 91-258.
    • (2001) The Alkaloids , vol.55 , pp. 91-258
    • Michael, J.P.1
  • 3
    • 0038106171 scopus 로고    scopus 로고
    • (c) Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 5
    • 0000188393 scopus 로고
    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart
    • For reviews, see: (a) de Koning, H.; Speckamp, W. N. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21b, pp 1953-2009.
    • (1995) Stereoselective Synthesis (Houben-Weyl) , vol.E21B , pp. 1953-2009
    • De Koning, H.1    Speckamp, W.N.2
  • 13
    • 0033550253 scopus 로고    scopus 로고
    • Diazoalkane C-H insertion reactions also occur preferentially at heteroatom-substituted C-H centers, see: (a) Sulikowski, G. A.; Lee, S. Tetrahedron Lett. 1999, 40, 8035-8038. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296-3305 and references thererin.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 8035-8038
    • Sulikowski, G.A.1    Lee, S.2
  • 14
    • 0000705205 scopus 로고
    • and references thererin
    • Diazoalkane C-H insertion reactions also occur preferentially at heteroatom-substituted C-H centers, see: (a) Sulikowski, G. A.; Lee, S. Tetrahedron Lett. 1999, 40, 8035-8038. (b) Wang, P.; Adams, J. J. Am. Chem. Soc. 1994, 116, 3296-3305 and references thererin.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3296-3305
    • Wang, P.1    Adams, J.2
  • 15
    • 0013399957 scopus 로고    scopus 로고
    • note
    • 2 centers. We have never observed transannular C-H insertion, however, with any cycloalkanol-derived sulfamate.
  • 16
    • 0013399958 scopus 로고    scopus 로고
    • note
    • 2, grade 643 (see the Supporting Information for details).
  • 17
    • 0037099190 scopus 로고    scopus 로고
    • Metal-acetylides have been employed in novel, highly selective addition reactions, see: (a) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538. (b) Frantz, D. E.; Fassler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373-381 and references therein.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2535-2538
    • Koradin, C.1    Polborn, K.2    Knochel, P.3
  • 18
    • 0038252959 scopus 로고    scopus 로고
    • and references therein
    • Metal-acetylides have been employed in novel, highly selective addition reactions, see: (a) Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538. (b) Frantz, D. E.; Fassler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373-381 and references therein.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 373-381
    • Frantz, D.E.1    Fassler, R.2    Tomooka, C.S.3    Carreira, E.M.4
  • 20
    • 0013395609 scopus 로고    scopus 로고
    • note
    • 1H NMR coupling constant, NOE, and/or X-ray analysis.
  • 22
    • 0013399325 scopus 로고    scopus 로고
    • note
    • 2) pseudoequatorially.
  • 24
    • 0000512831 scopus 로고    scopus 로고
    • and references therein
    • Carretero has reported the synthesis of 10, see: Carretero, J. C.; Arrayás, R. G. J. Org. Chem. 1998, 63. 2993-3005 and references therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 2993-3005
    • Carretero, J.C.1    Arrayás, R.G.2
  • 25
    • 0013349632 scopus 로고    scopus 로고
    • note
    • Details for the X-ray structure of 7 are in the Supporting Information.
  • 26
    • 0000171418 scopus 로고
    • 4 has been described previously, see: Okamoto, Y.; Kinoshita, T. Chem. Pharm. Bull. 1981, 29, 1165-1169. In our hands, these conditions proved uniquely effective for this rather unusual transformation.
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 1165-1169
    • Okamoto, Y.1    Kinoshita, T.2


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