First Synthesis of the Methyl syn 3-CF3-Isoserinate

Synlett

Volumn 1996, Issue 4, 1996, Pages 399-400

  Abouabdellah, Ahmed ^a   Bégué, Jean Pierre ^a   Bonnet Delpon, Danièle ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542529458     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5424     Document Type: Article

References (27)

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2. Gelb, M. H.; Svaren, J. P.; Abeles, R. B.; Biochemistry 1985, 24, 1813-1817 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. Thaisrivongs, S., Pals, D.T.; Turner, S.R. in Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch Ed., ACS Symposium Series 456, Washington D.C. 1991, pp 164-173 Smith, R.A.; Copp, L.J., Donnelly, S.L.; Spencer, R.W.; Krantz, A Biochemistry 1988, 27, 6568-6573. Stein, R.L.; Strimpler, A.M., Edwards, P.D.; Lewis, J.J.; Mauger, R.C.; Schwartz, J.A.; Stein, M.M.; Trainor, D.A.; Wildonger, R.A.; Zottola, M.A. Biochemistry 1987, 26, 2682-2689 Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767 Sham, H.L.; Stein, H.; Rempel, C.A.; Cohen, J. Plattner, J.J. FEBS Lett. 1987, 220, 299-301.
3. Gelb, M. H.; Svaren, J. P.; Abeles, R. B.; Biochemistry 1985, 24, 1813-1817 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. Thaisrivongs, S., Pals, D.T.; Turner, S.R. in Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch Ed., ACS Symposium Series 456, Washington D.C. 1991, pp 164-173 Smith, R.A.; Copp, L.J., Donnelly, S.L.; Spencer, R.W.; Krantz, A Biochemistry 1988, 27, 6568-6573. Stein, R.L.; Strimpler, A.M., Edwards, P.D.; Lewis, J.J.; Mauger, R.C.; Schwartz, J.A.; Stein, M.M.; Trainor, D.A.; Wildonger, R.A.; Zottola, M.A. Biochemistry 1987, 26, 2682-2689 Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767 Sham, H.L.; Stein, H.; Rempel, C.A.; Cohen, J. Plattner, J.J. FEBS Lett. 1987, 220, 299-301.
4. Gelb, M. H.; Svaren, J. P.; Abeles, R. B.; Biochemistry 1985, 24, 1813-1817 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. Thaisrivongs, S., Pals, D.T.; Turner, S.R. in Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch Ed., ACS Symposium Series 456, Washington D.C. 1991, pp 164-173 Smith, R.A.; Copp, L.J., Donnelly, S.L.; Spencer, R.W.; Krantz, A Biochemistry 1988, 27, 6568-6573. Stein, R.L.; Strimpler, A.M., Edwards, P.D.; Lewis, J.J.; Mauger, R.C.; Schwartz, J.A.; Stein, M.M.; Trainor, D.A.; Wildonger, R.A.; Zottola, M.A. Biochemistry 1987, 26, 2682-2689 Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767 Sham, H.L.; Stein, H.; Rempel, C.A.; Cohen, J. Plattner, J.J. FEBS Lett. 1987, 220, 299-301.
5. Gelb, M. H.; Svaren, J. P.; Abeles, R. B.; Biochemistry 1985, 24, 1813-1817 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. Thaisrivongs, S., Pals, D.T.; Turner, S.R. in Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch Ed., ACS Symposium Series 456, Washington D.C. 1991, pp 164-173 Smith, R.A.; Copp, L.J., Donnelly, S.L.; Spencer, R.W.; Krantz, A Biochemistry 1988, 27, 6568-6573. Stein, R.L.; Strimpler, A.M., Edwards, P.D.; Lewis, J.J.; Mauger, R.C.; Schwartz, J.A.; Stein, M.M.; Trainor, D.A.; Wildonger, R.A.; Zottola, M.A. Biochemistry 1987, 26, 2682-2689 Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767 Sham, H.L.; Stein, H.; Rempel, C.A.; Cohen, J. Plattner, J.J. FEBS Lett. 1987, 220, 299-301.
6. Gelb, M. H.; Svaren, J. P.; Abeles, R. B.; Biochemistry 1985, 24, 1813-1817 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. Thaisrivongs, S., Pals, D.T.; Turner, S.R. in Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch Ed., ACS Symposium Series 456, Washington D.C. 1991, pp 164-173 Smith, R.A.; Copp, L.J., Donnelly, S.L.; Spencer, R.W.; Krantz, A Biochemistry 1988, 27, 6568-6573. Stein, R.L.; Strimpler, A.M., Edwards, P.D.; Lewis, J.J.; Mauger, R.C.; Schwartz, J.A.; Stein, M.M.; Trainor, D.A.; Wildonger, R.A.; Zottola, M.A. Biochemistry 1987, 26, 2682-2689 Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767 Sham, H.L.; Stein, H.; Rempel, C.A.; Cohen, J. Plattner, J.J. FEBS Lett. 1987, 220, 299-301.
7. Gelb, M. H.; Svaren, J. P.; Abeles, R. B.; Biochemistry 1985, 24, 1813-1817 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. Thaisrivongs, S., Pals, D.T.; Turner, S.R. in Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch Ed., ACS Symposium Series 456, Washington D.C. 1991, pp 164-173 Smith, R.A.; Copp, L.J., Donnelly, S.L.; Spencer, R.W.; Krantz, A Biochemistry 1988, 27, 6568-6573. Stein, R.L.; Strimpler, A.M., Edwards, P.D.; Lewis, J.J.; Mauger, R.C.; Schwartz, J.A.; Stein, M.M.; Trainor, D.A.; Wildonger, R.A.; Zottola, M.A. Biochemistry 1987, 26, 2682-2689 Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767 Sham, H.L.; Stein, H.; Rempel, C.A.; Cohen, J. Plattner, J.J. FEBS Lett. 1987, 220, 299-301.
8. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138 Edwards, P.D. Tetrahedron Lett. 1992, 33, 4279-4282 Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6 Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668. Bégue, J.P., Bonnet-Delpon, D., Sdassi, H. Tetrahedron Lett. 1992, 33, 1879-1882. Bégué, J.P., Bonnet-Delpon, D.; Fischer-Durand N.; Reboud-Raveaux, M.; Amour, A Tetrahedron: Asymmetry 1994, 5, 1099-1110
9. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138 Edwards, P.D. Tetrahedron Lett. 1992, 33, 4279-4282 Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6 Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668. Bégue, J.P., Bonnet-Delpon, D., Sdassi, H. Tetrahedron Lett. 1992, 33, 1879-1882. Bégué, J.P., Bonnet-Delpon, D.; Fischer-Durand N.; Reboud-Raveaux, M.; Amour, A Tetrahedron: Asymmetry 1994, 5, 1099-1110
10. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138 Edwards, P.D. Tetrahedron Lett. 1992, 33, 4279-4282 Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6 Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668. Bégue, J.P., Bonnet-Delpon, D., Sdassi, H. Tetrahedron Lett. 1992, 33, 1879-1882. Bégué, J.P., Bonnet-Delpon, D.; Fischer-Durand N.; Reboud-Raveaux, M.; Amour, A Tetrahedron: Asymmetry 1994, 5, 1099-1110
11. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138 Edwards, P.D. Tetrahedron Lett. 1992, 33, 4279-4282 Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6 Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668. Bégue, J.P., Bonnet-Delpon, D., Sdassi, H. Tetrahedron Lett. 1992, 33, 1879-1882. Bégué, J.P., Bonnet-Delpon, D.; Fischer-Durand N.; Reboud-Raveaux, M.; Amour, A Tetrahedron: Asymmetry 1994, 5, 1099-1110
12. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138 Edwards, P.D. Tetrahedron Lett. 1992, 33, 4279-4282 Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6 Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668. Bégue, J.P., Bonnet-Delpon, D., Sdassi, H. Tetrahedron Lett. 1992, 33, 1879-1882. Bégué, J.P., Bonnet-Delpon, D.; Fischer-Durand N.; Reboud-Raveaux, M.; Amour, A Tetrahedron: Asymmetry 1994, 5, 1099-1110
13. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138 Edwards, P.D. Tetrahedron Lett. 1992, 33, 4279-4282 Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6 Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668. Bégue, J.P., Bonnet-Delpon, D., Sdassi, H. Tetrahedron Lett. 1992, 33, 1879-1882. Bégué, J.P., Bonnet-Delpon, D.; Fischer-Durand N.; Reboud-Raveaux, M.; Amour, A Tetrahedron: Asymmetry 1994, 5, 1099-1110
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24. It is worthnoting that, unlike cyclocondensation with lithium acetate enolate, cycloaddition with ketene cannot be performed from the mixture imine and the corresponding aminal which always accompanies the imine 5 in its preparation In our hands, the treatment of this mixture with LDA did not provide the pure imine 5. However, a careful distillation allowed the separation and the pure imine 5 was obtained in 60 % yield
25. 3 C, 61.54% , H, 4.59%, N, 4.0%. Found C, 60.77%. H, 4.91%, N, 3.81%
26. Browne, M , Burnett, D A , Caplen, M A , Chen, L Y , Clader, J W , Domalsky, M , Dugar, S , Pushpavanam, P , Sher, R ; Vaccaro, W , Viziano, M ; Zhao. H. Tetrahedron Lett. 1995, 36, 2555-2558.
27. 3), 172.4 (CO)