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Volumn 64, Issue 13, 1999, Pages 4920-4925

5-endo-trig radical cyclizations of bromomethyldimethylsilyl diisopropylpropargylic ethers. A highly diastereoselective access to functionalized cyclopentanes

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKENE; BROMOMETHYLDIMETHYLSILYL DIISOPROPYLPROPARGYL ETHER DERIVATIVE; CYCLOPENTANE DERIVATIVE; ETHER DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033603501     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904260     Document Type: Article
Times cited : (60)

References (45)
  • 10
    • 0028851974 scopus 로고
    • Mendenhall, G. D.; Protasiewicz, J. D.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1994, 116, 1718-1724. For related chemistry, see: Yamamoto, Y.; Ohno, M.; Eguchi, S. J. Am. Chem. Soc. 1995, 117, 9653-9661.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9653-9661
    • Yamamoto, Y.1    Ohno, M.2    Eguchi, S.3
  • 25
    • 0000899183 scopus 로고
    • For other examples 6-endo-dig cyclizations, see: (a) Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1891, 56, 5544-5553. (b) Khim, S.-K.; Cederstrom, E.; Ferri, D. C.; Mariano, P. S. Tetrahedron 1996, 52, 3195-3222. (c) Marco-Contelles, J.; Bernabé, M.; Ayala, D.; Sanchez, B. J. Org. Chem. 1994, 59, 1234- 1235. (d) Breithor, M.; Herden, U.; Hoffmann, H. M. R. Tetrahedron 1997, 53, 8401-8420.
    • (1891) J. Org. Chem. , vol.56 , pp. 5544-5553
    • Snider, B.B.1    Merritt, J.E.2    Dombroski, M.A.3    Buckman, B.O.4
  • 26
    • 0029918287 scopus 로고    scopus 로고
    • For other examples 6-endo-dig cyclizations, see: (a) Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1891, 56, 5544-5553. (b) Khim, S.-K.; Cederstrom, E.; Ferri, D. C.; Mariano, P. S. Tetrahedron 1996, 52, 3195-3222. (c) Marco-Contelles, J.; Bernabé, M.; Ayala, D.; Sanchez, B. J. Org. Chem. 1994, 59, 1234- 1235. (d) Breithor, M.; Herden, U.; Hoffmann, H. M. R. Tetrahedron 1997, 53, 8401-8420.
    • (1996) Tetrahedron , vol.52 , pp. 3195-3222
    • Khim, S.-K.1    Cederstrom, E.2    Ferri, D.C.3    Mariano, P.S.4
  • 27
    • 0028210231 scopus 로고
    • For other examples 6-endo-dig cyclizations, see: (a) Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1891, 56, 5544-5553. (b) Khim, S.-K.; Cederstrom, E.; Ferri, D. C.; Mariano, P. S. Tetrahedron 1996, 52, 3195-3222. (c) Marco-Contelles, J.; Bernabé, M.; Ayala, D.; Sanchez, B. J. Org. Chem. 1994, 59, 1234-1235. (d) Breithor, M.; Herden, U.; Hoffmann, H. M. R. Tetrahedron 1997, 53, 8401-8420.
    • (1994) J. Org. Chem. , vol.59 , pp. 1234-1235
    • Marco-Contelles, J.1    Bernabé, M.2    Ayala, D.3    Sanchez, B.4
  • 28
    • 0030944786 scopus 로고    scopus 로고
    • For other examples 6-endo-dig cyclizations, see: (a) Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1891, 56, 5544-5553. (b) Khim, S.-K.; Cederstrom, E.; Ferri, D. C.; Mariano, P. S. Tetrahedron 1996, 52, 3195-3222. (c) Marco-Contelles, J.; Bernabé, M.; Ayala, D.; Sanchez, B. J. Org. Chem. 1994, 59, 1234- 1235. (d) Breithor, M.; Herden, U.; Hoffmann, H. M. R. Tetrahedron 1997, 53, 8401-8420.
    • (1997) Tetrahedron , vol.53 , pp. 8401-8420
    • Breithor, M.1    Herden, U.2    Hoffmann, H.M.R.3
  • 29
    • 0001465664 scopus 로고
    • With a dimethyl group, this process is not observed, see: Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2255-2256
    • Magnol, E.1    Malacria, M.2
  • 34
    • 85012331749 scopus 로고
    • 3SnD) for the reduction of the tert-butyl radical is 2.74; see: Carlsson, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1968, 90, 7047-7055.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 7047-7055
    • Carlsson, D.J.1    Ingold, K.U.2
  • 36
    • 33748608306 scopus 로고    scopus 로고
    • For studies concerning the competition between 4-exo-trig and 5-endo-trig cyclization on styryl systems, see: Ikeda, M.; Ohtani, S.; Yamamoto, T.; Sato, T.; Ishibashi, H. J. Chem. Soc., Perkin Trans. 1 1998, 1763-1768. See also: D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1997, 38, 1829-1832.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1763-1768
    • Ikeda, M.1    Ohtani, S.2    Yamamoto, T.3    Sato, T.4    Ishibashi, H.5
  • 37
    • 0031562449 scopus 로고    scopus 로고
    • For studies concerning the competition between 4-exo-trig and 5-endo-trig cyclization on styryl systems, see: Ikeda, M.; Ohtani, S.; Yamamoto, T.; Sato, T.; Ishibashi, H. J. Chem. Soc., Perkin Trans. 1 1998, 1763-1768. See also: D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1997, 38, 1829-1832.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1829-1832
    • D'Annibale, A.1    Pesce, A.2    Resta, S.3    Trogolo, C.4
  • 41
    • 0000981272 scopus 로고    scopus 로고
    • H-P coupling constants on allylic phosphonates obtained via a base-catalyzed isomerization of the corresponding vinylphosphonates, see: (a) Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572-3574. (b) Al Badri, H. Ph.D. Dissertation, Université de Rouen, 1996.
    • (1993) J. Org. Chem. , vol.58 , pp. 3572-3574
    • Kiddle, J.J.1    Babler, J.H.2
  • 42
    • 0000981272 scopus 로고    scopus 로고
    • Ph.D. Dissertation, Université de Rouen
    • H-P coupling constants on allylic phosphonates obtained via a base-catalyzed isomerization of the corresponding vinylphosphonates, see: (a) Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572-3574. (b) Al Badri, H. Ph.D. Dissertation, Université de Rouen, 1996.
    • (1996)
    • Al Badri, H.1
  • 43
    • 0345660738 scopus 로고    scopus 로고
    • Some deuterium was incorporated on the methyl of the phosphine oxide moiety of 2im
    • Some deuterium was incorporated on the methyl of the phosphine oxide moiety of 2im.


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