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Volumn 52, Issue 9, 1996, Pages 3327-3338

Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

Author keywords

enamide; epoxidation; imidate; indinavir; iodohydrin

Indexed keywords

AMIDE; ANTIVIRUS AGENT; EPOXIDE; INDINAVIR;

EID: 0030065870     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01114-5     Document Type: Article
Times cited : (42)

References (30)
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    • Moon, H.; Eisenberg, S.W.E.; Wilson, M.E.; Schore, N.E.; Kurth, M.J. J. Org. Chem. 1994, 59, 6504-6505. For other examples of iodolactone formation via iodoimidate type intermediates, see: Yokamatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728-729. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1992, 33, 6999-7002. Takano, E.; Murakata, C.; Imamura, Y.; Tamura, N.; Ogasawara, K. Heterocycles, 1981, 16, 1291-1294. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175-3178. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291-1294. Hart, D.J.; Huang, H.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1994) J. Org. Chem. , vol.59 , pp. 6504-6505
    • Moon, H.1    Eisenberg, S.W.E.2    Wilson, M.E.3    Schore, N.E.4    Kurth, M.J.5
  • 3
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    • Moon, H.; Eisenberg, S.W.E.; Wilson, M.E.; Schore, N.E.; Kurth, M.J. J. Org. Chem. 1994, 59, 6504-6505. For other examples of iodolactone formation via iodoimidate type intermediates, see: Yokamatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728-729. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1992, 33, 6999-7002. Takano, E.; Murakata, C.; Imamura, Y.; Tamura, N.; Ogasawara, K. Heterocycles, 1981, 16, 1291-1294. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175-3178. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291-1294. Hart, D.J.; Huang, H.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 728-729
    • Yokamatsu, T.I.H.1    Shibuya, S.2
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    • Moon, H.; Eisenberg, S.W.E.; Wilson, M.E.; Schore, N.E.; Kurth, M.J. J. Org. Chem. 1994, 59, 6504-6505. For other examples of iodolactone formation via iodoimidate type intermediates, see: Yokamatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728-729. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1992, 33, 6999-7002. Takano, E.; Murakata, C.; Imamura, Y.; Tamura, N.; Ogasawara, K. Heterocycles, 1981, 16, 1291-1294. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175-3178. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291-1294. Hart, D.J.; Huang, H.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6999-7002
    • Yokomatsu, T.1    Iwasawa, H.2    Shibuya, S.3
  • 5
    • 0024449383 scopus 로고
    • Moon, H.; Eisenberg, S.W.E.; Wilson, M.E.; Schore, N.E.; Kurth, M.J. J. Org. Chem. 1994, 59, 6504-6505. For other examples of iodolactone formation via iodoimidate type intermediates, see: Yokamatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728-729. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1992, 33, 6999-7002. Takano, E.; Murakata, C.; Imamura, Y.; Tamura, N.; Ogasawara, K. Heterocycles, 1981, 16, 1291-1294. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175-3178. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291-1294. Hart, D.J.; Huang, H.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1981) Heterocycles , vol.16 , pp. 1291-1294
    • Takano, E.1    Murakata, C.2    Imamura, Y.3    Tamura, N.4    Ogasawara, K.5
  • 6
    • 0025307498 scopus 로고
    • Moon, H.; Eisenberg, S.W.E.; Wilson, M.E.; Schore, N.E.; Kurth, M.J. J. Org. Chem. 1994, 59, 6504-6505. For other examples of iodolactone formation via iodoimidate type intermediates, see: Yokamatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728-729. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1992, 33, 6999-7002. Takano, E.; Murakata, C.; Imamura, Y.; Tamura, N.; Ogasawara, K. Heterocycles, 1981, 16, 1291-1294. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175-3178. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291-1294. Hart, D.J.; Huang, H.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3175-3178
    • Fuji, K.1    Node, M.2    Naniwa, Y.3    Kawabata, T.4
  • 7
    • 0024449383 scopus 로고
    • Moon, H.; Eisenberg, S.W.E.; Wilson, M.E.; Schore, N.E.; Kurth, M.J. J. Org. Chem. 1994, 59, 6504-6505. For other examples of iodolactone formation via iodoimidate type intermediates, see: Yokamatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728-729. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1992, 33, 6999-7002. Takano, E.; Murakata, C.; Imamura, Y.; Tamura, N.; Ogasawara, K. Heterocycles, 1981, 16, 1291-1294. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175-3178. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291-1294. Hart, D.J.; Huang, H.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1981) Heterocycles , vol.16 , pp. 1291-1294
    • Takano, S.1    Murakata, C.2    Imamura, Y.3
  • 8
    • 0024449383 scopus 로고
    • Moon, H.; Eisenberg, S.W.E.; Wilson, M.E.; Schore, N.E.; Kurth, M.J. J. Org. Chem. 1994, 59, 6504-6505. For other examples of iodolactone formation via iodoimidate type intermediates, see: Yokamatsu, T.; Iwasawa, H.; Shibuya, S. J. Chem. Soc., Chem. Commun. 1992, 728-729. Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1992, 33, 6999-7002. Takano, E.; Murakata, C.; Imamura, Y.; Tamura, N.; Ogasawara, K. Heterocycles, 1981, 16, 1291-1294. Fuji, K.; Node, M.; Naniwa, Y.; Kawabata, T. Tetrahedron Lett. 1990, 31, 3175-3178. Takano, S.; Murakata, C.; Imamura, Y. Heterocycles 1981, 16, 1291-1294. Hart, D.J.; Huang, H.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7507-7519
    • Hart, D.J.1    Huang, H.2    Krishnamurthy, R.3    Schwartz, T.4
  • 24
    • 85030187676 scopus 로고    scopus 로고
    • note
    • 2, aqueous THF). This apparent disparity in product formation at similar pH may be attributed to the biphasic nature of the NIS/IPAc/water system.
  • 28
    • 85030187718 scopus 로고    scopus 로고
    • note
    • 13C). Attempted isolation of this product was not successful. The oxazoline 11 was presumed to bear the 2,4-syn stereochemistry; however, this was not confirmed due its instability.
  • 29
    • 0028157516 scopus 로고
    • For a review on the formation and chemistry of 2-oxazolines, see: Grant, T.G.; Meyers, A. I. Tetrahedron 1994, 50, 2297-2360.
    • (1994) Tetrahedron , vol.50 , pp. 2297-2360
    • Grant, T.G.1    Meyers, A.I.2


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