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Volumn 62, Issue 9, 1997, Pages 2877-2884

2-Substituted 2,3-Dhiydro-4H-1,3-benzoxazin-4-ones: Novel Auxiliaries for Stereoselective Synthesis of 1-β-Methylcarbapenems

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM DERIVATIVE;

EID: 0030908562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961866j     Document Type: Article
Times cited : (39)

References (43)
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    • See, for example: (a) Horrom, B. W.; Zaugg, H. E. J. Am. Chem. Soc. 1950, 72, 721-724. For the base-catalized reactions, see: (b) Gammill, R. B. J. Org. Chem. 1981, 46, 3340-3342.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 721-724
    • Horrom, B.W.1    Zaugg, H.E.2
  • 15
    • 0001058422 scopus 로고
    • See, for example: (a) Horrom, B. W.; Zaugg, H. E. J. Am. Chem. Soc. 1950, 72, 721-724. For the base-catalized reactions, see: (b) Gammill, R. B. J. Org. Chem. 1981, 46, 3340-3342.
    • (1981) J. Org. Chem. , vol.46 , pp. 3340-3342
    • Gammill, R.B.1
  • 20
    • 84889553902 scopus 로고    scopus 로고
    • The author has deposited X-ray data with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK
    • The author has deposited X-ray data with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 21
    • 26844464651 scopus 로고
    • Because the Reformatsky reagent is very susceptible to hydrolysis under the silylation conditions, it was not possible to obtain the Z silyl enol ether 14e without concomitant formation of the reduced product 15e. For the related silylation of the Reformatsky reagents, see: (a) Slougui, N.; Rosseau, G. Synth. Commun. 1987, 17, 1-11.
    • (1987) Synth. Commun. , vol.17 , pp. 1-11
    • Slougui, N.1    Rosseau, G.2
  • 24
    • 84855209169 scopus 로고
    • (a) For review, see: Furstner, A. Synthesis 1989, 571-590. (b) Moriwake, T. J. Org. Chem. 1966, 31, 983-985. (c) Ding, Y.; Zhao, G. J. Chem. Soc., Chem. Commun. 1992, 941-942.
    • (1989) Synthesis , pp. 571-590
    • Furstner, A.1
  • 25
    • 33947335173 scopus 로고
    • (a) For review, see: Furstner, A. Synthesis 1989, 571-590. (b) Moriwake, T. J. Org. Chem. 1966, 31, 983-985. (c) Ding, Y.; Zhao, G. J. Chem. Soc., Chem. Commun. 1992, 941-942.
    • (1966) J. Org. Chem. , vol.31 , pp. 983-985
    • Moriwake, T.1
  • 26
    • 37049089255 scopus 로고
    • (a) For review, see: Furstner, A. Synthesis 1989, 571-590. (b) Moriwake, T. J. Org. Chem. 1966, 31, 983-985. (c) Ding, Y.; Zhao, G. J. Chem. Soc., Chem. Commun. 1992, 941-942.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 941-942
    • Ding, Y.1    Zhao, G.2
  • 32
    • 84889523912 scopus 로고    scopus 로고
    • For the Diekmann-type cyclization with alkyl halide as a scavenger, see reference 9d
    • For the Diekmann-type cyclization with alkyl halide as a scavenger, see reference 9d.
  • 33
    • 84889505165 scopus 로고    scopus 로고
    • Attempts to isolate the silyl derivative 13b prior to aqueous workup were unsuccessful
    • Attempts to isolate the silyl derivative 13b prior to aqueous workup were unsuccessful.
  • 35
    • 85086289570 scopus 로고    scopus 로고
    • 10
    • 10
  • 36
    • 84889547507 scopus 로고    scopus 로고
    • For example, see: reference 3
    • For example, see: reference 3.
  • 40
    • 84889500393 scopus 로고    scopus 로고
    • Japanese Patent 06,065,195 Mar 8, 1994
    • After completion of our work, a similar transformation using pyrrolidones was reported in a patent literature: Asai, H.; Suzuki, K.; Nakada, J.; Ishikawa, M.; Nakagawa, S. Japanese Patent 06,065,195 Mar 8, 1994. Chem. Abstr. 1994, 121, 35188m. For a related method, see: Sunakawa, J.; Tamoto, K. Japanese Patent 02,178,262 Jul 11, 1990. Chem. Abstr. 1991, 114, 23689t.
    • Asai, H.1    Suzuki, K.2    Nakada, J.3    Ishikawa, M.4    Nakagawa, S.5
  • 41
    • 84889549680 scopus 로고
    • After completion of our work, a similar transformation using pyrrolidones was reported in a patent literature: Asai, H.; Suzuki, K.; Nakada, J.; Ishikawa, M.; Nakagawa, S. Japanese Patent 06,065,195 Mar 8, 1994. Chem. Abstr. 1994, 121, 35188m. For a related method, see: Sunakawa, J.; Tamoto, K. Japanese Patent 02,178,262 Jul 11, 1990. Chem. Abstr. 1991, 114, 23689t.
    • (1994) Chem. Abstr. , vol.121
  • 42
    • 84889543088 scopus 로고    scopus 로고
    • Japanese Patent 02,178,262 Jul 11, 1990
    • After completion of our work, a similar transformation using pyrrolidones was reported in a patent literature: Asai, H.; Suzuki, K.; Nakada, J.; Ishikawa, M.; Nakagawa, S. Japanese Patent 06,065,195 Mar 8, 1994. Chem. Abstr. 1994, 121, 35188m. For a related method, see: Sunakawa, J.; Tamoto, K. Japanese Patent 02,178,262 Jul 11, 1990. Chem. Abstr. 1991, 114, 23689t.
    • Sunakawa, J.1    Tamoto, K.2
  • 43
    • 84889506265 scopus 로고
    • After completion of our work, a similar transformation using pyrrolidones was reported in a patent literature: Asai, H.; Suzuki, K.; Nakada, J.; Ishikawa, M.; Nakagawa, S. Japanese Patent 06,065,195 Mar 8, 1994. Chem. Abstr. 1994, 121, 35188m. For a related method, see: Sunakawa, J.; Tamoto, K. Japanese Patent 02,178,262 Jul 11, 1990. Chem. Abstr. 1991, 114, 23689t.
    • (1991) Chem. Abstr. , vol.114


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