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Volumn 61, Issue 7, 1996, Pages 2428-2440

Practical syntheses of enantiomerically enriched γ-lactones and γ-hydroxy ketones by the alkylation of pseudoephedrine amides with epoxides and their derivatives

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTONE DERIVATIVE; PSEUDOEPHEDRINE; PSEUDOEPHEDRINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030010210     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952032o     Document Type: Article
Times cited : (108)

References (45)
  • 7
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    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 7
    • For reviews, see also. (d) Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 7, p 193. (e) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis: Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 8, p 247.
    • (1985) Asymmetric Synthesis , vol.5 , pp. 193
    • Rossiter, B.E.1
  • 8
    • 84941216140 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York, Chapter 8
    • For reviews, see also. (d) Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 7, p 193. (e) Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis: Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 8, p 247.
    • (1985) Asymmetric Synthesis , vol.5 , pp. 247
    • Finn, M.G.1    Sharpless, K.B.2
  • 9
    • 0000155341 scopus 로고
    • and references therein
    • Successful enolate-epoxide bond constructions typically employ stabilized enolates (e.g., malonate derivatives) at elevated reaction temperatures or, in the case of monoester and monoketone enolates, utilize Lewis-acidic additives: (a) Danishefsky, S.; Kitahara, T.; Tsai, M.; Dynak, J. J. Org. Chem. 1976, 41, 1669; and references therein. (b) Sturm, T.; Marlewski, A. E.; Rezenka, D. S.; Taylor, S. K. J. Org. Chem. 1989, 54, 2039. (c) Chini. M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (d) Smith, A. E., III; Pasternak, A.; Yokoyama, A.; Hirschmann, R. Tetrahedron Lett. 1994, 35, 8977.
    • (1976) J. Org. Chem. , vol.41 , pp. 1669
    • Danishefsky, S.1    Kitahara, T.2    Tsai, M.3    Dynak, J.4
  • 10
    • 0000993114 scopus 로고
    • Successful enolate-epoxide bond constructions typically employ stabilized enolates (e.g., malonate derivatives) at elevated reaction temperatures or, in the case of monoester and monoketone enolates, utilize Lewis-acidic additives: (a) Danishefsky, S.; Kitahara, T.; Tsai, M.; Dynak, J. J. Org. Chem. 1976, 41, 1669; and references therein. (b) Sturm, T.; Marlewski, A. E.; Rezenka, D. S.; Taylor, S. K. J. Org. Chem. 1989, 54, 2039. (c) Chini. M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (d) Smith, A. E., III; Pasternak, A.; Yokoyama, A.; Hirschmann, R. Tetrahedron Lett. 1994, 35, 8977.
    • (1989) J. Org. Chem. , vol.54 , pp. 2039
    • Sturm, T.1    Marlewski, A.E.2    Rezenka, D.S.3    Taylor, S.K.4
  • 11
    • 0026334190 scopus 로고
    • Successful enolate-epoxide bond constructions typically employ stabilized enolates (e.g., malonate derivatives) at elevated reaction temperatures or, in the case of monoester and monoketone enolates, utilize Lewis-acidic additives: (a) Danishefsky, S.; Kitahara, T.; Tsai, M.; Dynak, J. J. Org. Chem. 1976, 41, 1669; and references therein. (b) Sturm, T.; Marlewski, A. E.; Rezenka, D. S.; Taylor, S. K. J. Org. Chem. 1989, 54, 2039. (c) Chini. M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (d) Smith, A. E., III; Pasternak, A.; Yokoyama, A.; Hirschmann, R. Tetrahedron Lett. 1994, 35, 8977.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 7583
    • Chini, M.1    Crotti, P.2    Favero, L.3    Pineschi, M.4
  • 12
    • 0028006932 scopus 로고
    • Successful enolate-epoxide bond constructions typically employ stabilized enolates (e.g., malonate derivatives) at elevated reaction temperatures or, in the case of monoester and monoketone enolates, utilize Lewis-acidic additives: (a) Danishefsky, S.; Kitahara, T.; Tsai, M.; Dynak, J. J. Org. Chem. 1976, 41, 1669; and references therein. (b) Sturm, T.; Marlewski, A. E.; Rezenka, D. S.; Taylor, S. K. J. Org. Chem. 1989, 54, 2039. (c) Chini. M.; Crotti, P.; Favero, L.; Pineschi, M. Tetrahedron Lett. 1991, 32, 7583. (d) Smith, A. E., III; Pasternak, A.; Yokoyama, A.; Hirschmann, R. Tetrahedron Lett. 1994, 35, 8977.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8977
    • Smith III, A.E.1    Pasternak, A.2    Yokoyama, A.3    Hirschmann, R.4
  • 20
    • 0015512524 scopus 로고
    • For the reaction of carboxylate enolates with epoxides, see: (h) Creger, P. L. J. Org. Chem. 1972, 37, 1907. For the reaction of chiral oxazoline anions with epoxides, see: (i) Meyers, A. I.; Mihelich, E. D. J. Org. Chem. 1975, 40, 1187.
    • (1972) J. Org. Chem. , vol.37 , pp. 1907
    • Creger, P.L.1
  • 21
    • 15844414237 scopus 로고
    • For the reaction of carboxylate enolates with epoxides, see: (h) Creger, P. L. J. Org. Chem. 1972, 37, 1907. For the reaction of chiral oxazoline anions with epoxides, see: (i) Meyers, A. I.; Mihelich, E. D. J. Org. Chem. 1975, 40, 1187.
    • (1975) J. Org. Chem. , vol.40 , pp. 1187
    • Meyers, A.I.1    Mihelich, E.D.2


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