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Volumn 110, Issue 19, 1988, Pages 6487-6491

A mechanistic study of the mitsunobu esterification reaction

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Indexed keywords


EID: 0000951044     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00227a032     Document Type: Article
Times cited : (210)

References (12)
  • 1
    • 0001633349 scopus 로고
    • (b) Mitsunobu, O. Synthesis 1981, 1–28
    • Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380–2382. (b) Mitsunobu, O. Synthesis 1981, 1–28.
    • (1967) Bull. Chem. Soc. Jpn. , vol.40 , pp. 2380-2382
    • Mitsunobu, O.1    Yamada, M.2
  • 2
    • 49149144714 scopus 로고
    • Thienamycin synthesis using hydroxyl inversion 1A to IB (b) Melillo, D. G.; Liu, T.; Ryan, K.; Sletzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913. (c) Shinkai, I.; Liu, T.; Reamer, R. A.; Sletzinger, M. Tetrahedron Lett. 1982, 23, 4899–4902. (d) Sletzinger, M.; Liu, T.; Reamer, R. A.; Shinkai, I. Tetrahdedron Lett. 1980, 21, 4221–4224
    • Thienamycin synthesis using hydroxyl inversion 1A to IB: (a) Melillo, D. G.; Shinkai, I.; Liu, T.; Ryan, K.; Sletzinger, M. Tetrahedron Lett. 1980, 21, 2783. (b) Melillo, D. G.; Liu, T.; Ryan, K.; Sletzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913. (c) Shinkai, I.; Liu, T.; Reamer, R. A.; Sletzinger, M. Tetrahedron Lett. 1982, 23, 4899–4902. (d) Sletzinger, M.; Liu, T.; Reamer, R. A.; Shinkai, I. Tetrahdedron Lett. 1980, 21, 4221–4224.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 2783
    • Melillo, D.G.1    Shinkai, I.2    Liu, T.3    Ryan, K.4    Sletzinger, M.5
  • 3
    • 85022509196 scopus 로고    scopus 로고
    • with diisopropyl azodi-carboxylate (DIAD) instead of the ethyl ester (DEAD) because the former was considered a safer compound and was more readily available
    • The inversion reactions were originally run in these laboratories on a large scale Thus, our studies centered on the use of DIAD instead of DEAD. Recent work indicates little difference between the two reagents
    • The inversion reactions were originally run in these laboratories on a large scale (G. Gal, G. G. Hazen, R. P. Volante) with diisopropyl azodi-carboxylate (DIAD) instead of the ethyl ester (DEAD) because the former was considered a safer compound and was more readily available. Thus, our studies centered on the use of DIAD instead of DEAD. Recent work indicates little difference between the two reagents.
    • Gal, G.1    Hazen, G.G.2    Volante, R.P.3
  • 4
    • 0001327369 scopus 로고
    • (b) Grochowski, E.; Hilton, B. D.; Kupper, R. J.; Michejda, C. J. J. Am. Chem. Soc. 1982, 104, 6876-6877. (c) Von Itzstein, M.; Jenkins, I. D. Aust. J. Chem. 1983, 36, 557–563. (d) Guthrie, R. D.; Jenkins, I. D. Aust. J. Chem. 1982, 35, 767–774
    • Adam, W.; Narita, N.; Nishizawa, Y. J. Am. Chem. Soc. 1984, 106, 1843–1845. (b) Grochowski, E.; Hilton, B. D.; Kupper, R. J.; Michejda, C. J. J. Am. Chem. Soc. 1982, 104, 6876-6877. (c) Von Itzstein, M.; Jenkins, I. D. Aust. J. Chem. 1983, 36, 557–563. (d) Guthrie, R. D.; Jenkins, I. D. Aust. J. Chem. 1982, 35, 767–774.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 1843-1845
    • Adam, W.1    Narita, N.2    Nishizawa, Y.3
  • 7
    • 0001607196 scopus 로고
    • (b) Hojo, M.; Imai, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1963–1967
    • Chantooni, M. K., Jr.; Kolthoff, I. M. J. Am. Chem. Soc. 1970, 92, 7025–7030. (b) Hojo, M.; Imai, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1963–1967.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 7025-7030
    • Chantooni, M.K.1    Kolthoff, I.M.2
  • 8
    • 84985216731 scopus 로고
    • Oxyphosphonium ions have been isolated and characterized from Mitsunobu reactions
    • Oxyphosphonium ions have been isolated and characterized from Mitsunobu reactions: Kunz, H.; Schmidt, P. Justus Liebigs Ann. Chem. 1982, 1245–1260.
    • (1982) Justus Liebigs Ann. Chem. , pp. 1245-1260
    • Kunz, H.1    Schmidt, P.2
  • 9
    • 0003887404 scopus 로고
    • Mechanism and Theory in Organic Chemistry
    • 1st ed.; Harper and Row: New York
    • Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 1st ed.; Harper and Row: New York, 1976; p 153.
    • (1976) , pp. 153
    • Lowry, T.H.1    Richardson, K.S.2
  • 12
    • 0004142603 scopus 로고
    • The Organic Chemistry of Electrolyte Solutions
    • Wiley: New York
    • Gordon, J. E. The Organic Chemistry of Electrolyte Solutions; Wiley: New York, 1975; pp 94–105.
    • (1975) , pp. 94-105
    • Gordon, J.E.1


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