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Volumn 62, Issue 25, 1997, Pages 8826-8833

Diastereoselective Synthesis of the Nonracemic Methyl syn-(3-Fluoroalkyl)isoserinates

Author keywords

[No Author keywords available]

Indexed keywords

ISOSERINE; METHYL (3 FLUOROALKYL)ISOSERINATE; UNCLASSIFIED DRUG;

EID: 0031438735     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (85)

References (31)
  • 1
    • 0023191615 scopus 로고
    • Sham, H. L.; Stein, H.; Rempel, C. A.; Cohen J.; Plattner, J. J. FEBS Lett. 1987, 220, 299-301. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1988, 29, 4665-4668. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo Jr, E. W. J. Med. Chem. 1993, 36, 2431-2447. Giordano, C.; Gallina, C., Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1989, 24, 357-362. Smith, R. A.; Copp, L. J.; Donnelly, S. L.; Spencer, R. W.; Krantz, A. Biochemistry 1988, 27, 6568-6573.
    • (1987) FEBS Lett. , vol.220 , pp. 299-301
    • Sham, H.L.1    Stein, H.2    Rempel, C.A.3    Cohen, J.4    Plattner, J.J.5
  • 2
    • 0023686354 scopus 로고
    • Sham, H. L.; Stein, H.; Rempel, C. A.; Cohen J.; Plattner, J. J. FEBS Lett. 1987, 220, 299-301. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1988, 29, 4665-4668. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo Jr, E. W. J. Med. Chem. 1993, 36, 2431-2447. Giordano, C.; Gallina, C., Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1989, 24, 357-362. Smith, R. A.; Copp, L. J.; Donnelly, S. L.; Spencer, R. W.; Krantz, A. Biochemistry 1988, 27, 6568-6573.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4665-4668
    • Patel, D.V.1    Rielly-Gauvin, K.2    Ryono, D.E.3
  • 3
    • 0027172371 scopus 로고
    • Sham, H. L.; Stein, H.; Rempel, C. A.; Cohen J.; Plattner, J. J. FEBS Lett. 1987, 220, 299-301. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1988, 29, 4665-4668. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo Jr, E. W. J. Med. Chem. 1993, 36, 2431-2447. Giordano, C.; Gallina, C., Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1989, 24, 357-362. Smith, R. A.; Copp, L. J.; Donnelly, S. L.; Spencer, R. W.; Krantz, A. Biochemistry 1988, 27, 6568-6573.
    • (1993) J. Med. Chem. , vol.36 , pp. 2431-2447
    • Patel, D.V.1    Rielly-Gauvin, K.2    Ryono, D.E.3    Free, C.A.4    Smith, S.A.5    Petrillo Jr., E.W.6
  • 4
    • 0024434402 scopus 로고
    • Sham, H. L.; Stein, H.; Rempel, C. A.; Cohen J.; Plattner, J. J. FEBS Lett. 1987, 220, 299-301. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1988, 29, 4665-4668. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo Jr, E. W. J. Med. Chem. 1993, 36, 2431-2447. Giordano, C.; Gallina, C., Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1989, 24, 357-362. Smith, R. A.; Copp, L. J.; Donnelly, S. L.; Spencer, R. W.; Krantz, A. Biochemistry 1988, 27, 6568-6573.
    • (1989) Eur. J. Med. Chem. , vol.24 , pp. 357-362
    • Giordano, C.1    Gallina, C.2    Consalvi, V.3    Scandurra, R.4
  • 5
    • 0023721950 scopus 로고
    • Sham, H. L.; Stein, H.; Rempel, C. A.; Cohen J.; Plattner, J. J. FEBS Lett. 1987, 220, 299-301. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1988, 29, 4665-4668. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo Jr, E. W. J. Med. Chem. 1993, 36, 2431-2447. Giordano, C.; Gallina, C., Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1989, 24, 357-362. Smith, R. A.; Copp, L. J.; Donnelly, S. L.; Spencer, R. W.; Krantz, A. Biochemistry 1988, 27, 6568-6573.
    • (1988) Biochemistry , vol.27 , pp. 6568-6573
    • Smith, R.A.1    Copp, L.J.2    Donnelly, S.L.3    Spencer, R.W.4    Krantz, A.5
  • 9
    • 0021982978 scopus 로고
    • Rich, D. H. J. Med. Chem. 1985, 28, 263. Moore, M. L.; Dreyer, G. B. Perspect. Drug Dis. Design 1093, 1, 85-108. Gait, M. J.; Karn, J. TIBTECH 1995, 13, 430-437.
    • (1985) J. Med. Chem. , vol.28 , pp. 263
    • Rich, D.H.1
  • 10
    • 0001872895 scopus 로고
    • Rich, D. H. J. Med. Chem. 1985, 28, 263. Moore, M. L.; Dreyer, G. B. Perspect. Drug Dis. Design 1093, 1, 85-108. Gait, M. J.; Karn, J. TIBTECH 1995, 13, 430-437.
    • (1093) Perspect. Drug Dis. Design , vol.1 , pp. 85-108
    • Moore, M.L.1    Dreyer, G.B.2
  • 11
    • 0028971801 scopus 로고
    • Rich, D. H. J. Med. Chem. 1985, 28, 263. Moore, M. L.; Dreyer, G. B. Perspect. Drug Dis. Design 1093, 1, 85-108. Gait, M. J.; Karn, J. TIBTECH 1995, 13, 430-437.
    • (1995) TIBTECH , vol.13 , pp. 430-437
    • Gait, M.J.1    Karn, J.2
  • 15
    • 0000766975 scopus 로고
    • Georg, G. I., Ed.; VCH Publishers: New York; and references therein
    • (a) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1992; pp 295-368 and references therein.
    • (1992) The Organic Chemistry of Β-Lactams , pp. 295-368
    • Georg, G.I.1    Ravikumar, V.T.2
  • 16
    • 0002102562 scopus 로고
    • Georg, G. I., Ed.; VCH Publishers: New York
    • (b) Ojima, I. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1992; pp 197-255.
    • (1992) The Organic Chemistry of Β-Lactams , pp. 197-255
    • Ojima, I.1
  • 18
    • 1542441396 scopus 로고    scopus 로고
    • note
    • It is worth noting that, unlike cyclocondensation with lithium acetate enolate, cycloaddition with ketene cannot be performed from the mixture imine and the corresponding amino ester, which always accompanies the imine 7a in its preparation. In our hands, the treatment of this mixture with LDA did not provide the pure imine 7a. However, a careful distillation allowed the separation and the pure imine 7a was obtained in 60% yield.
  • 23
    • 0028008520 scopus 로고
    • Hashimoto, Y.; Kai, A.; Saigo, K. Tetrahedron Lett. 1995, 48, 8821-8824. Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 47, 381-384.
    • (1994) Tetrahedron Lett. , vol.47 , pp. 381-384
    • Georg, G.I.1    Wu, Z.2
  • 26
    • 33845183324 scopus 로고
    • For reviews: (c) Hart, D. J.; Ha, D. C. Chem. Rev. (Washington, D.C.) 1989, 89, 1447. (d) Ojima, I. Acc. Chem. Res 1995, 28, 383-389 and references cited herein.
    • (1989) Chem. Rev. (Washington, D.C.) , vol.89 , pp. 1447
    • Hart, D.J.1    Ha, D.C.2
  • 27
    • 0000096261 scopus 로고
    • and references cited herein
    • For reviews: (c) Hart, D. J.; Ha, D. C. Chem. Rev. (Washington, D.C.) 1989, 89, 1447. (d) Ojima, I. Acc. Chem. Res 1995, 28, 383-389 and references cited herein.
    • (1995) Acc. Chem. Res , vol.28 , pp. 383-389
    • Ojima, I.1
  • 31
    • 1542441398 scopus 로고    scopus 로고
    • note
    • The authors have deposited atomic coordinates for this structure 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.