A Palladium Catalyzed Synthesis of Precursors of 2-Amino-5-Phosphonopentanoic Acid and Related Compounds

Synlett

Volumn 1997, Issue 4, 1997, Pages 384-386

  Attolini, Mireille ^a   Maffei, Michel ^a   Principato, Bruno ^a   Peiffer, Gilbert ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002292597     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-794     Document Type: Article

References (24)

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2. Harde, C.; Neff, K.H.; Gerblig, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett., 1994, 4, 273.
3. Whitten, J.P.; Cube, R.V.; Baron, B.M.; McDonald, I.A. Bioorg. Med. Chem. Lett., 1993, 3, 19. Whitten, J.P.; Baron, B.M.; McDonald, I.A. Ibid., 1993, 3, 26. Rudisill, D.E.; Whitten, J.P. Synthesis, 1994, 851.
4. Whitten, J.P.; Cube, R.V.; Baron, B.M.; McDonald, I.A. Bioorg. Med. Chem. Lett., 1993, 3, 19. Whitten, J.P.; Baron, B.M.; McDonald, I.A. Ibid., 1993, 3, 26. Rudisill, D.E.; Whitten, J.P. Synthesis, 1994, 851.
5. Whitten, J.P.; Cube, R.V.; Baron, B.M.; McDonald, I.A. Bioorg. Med. Chem. Lett., 1993, 3, 19. Whitten, J.P.; Baron, B.M.; McDonald, I.A. Ibid., 1993, 3, 26. Rudisill, D.E.; Whitten, J.P. Synthesis, 1994, 851.
6. Principato, B.; Maffei, M.; Siv, C.; Buono, G.; Peiffer, G. Tetrahedron, 1996, 52, 2087.
7. See for leading references : Ferroud, D.; Genêt, J.P.; Kiolle, R. Tetrahedron Lett.. 1986, 27, 23. Genêt, J.P.; Ferroud, D.; Montes, J.R. Ibid., 1986, 27, 4573. Genêt, J.P; Juge, S.; Mallart, S.; Ruiz Montes, J.; Levif, G. Tetrahedron. 1988, 44, 5263.
8. See for leading references : Ferroud, D.; Genêt, J.P.; Kiolle, R. Tetrahedron Lett.. 1986, 27, 23. Genêt, J.P.; Ferroud, D.; Montes, J.R. Ibid., 1986, 27, 4573. Genêt, J.P; Juge, S.; Mallart, S.; Ruiz Montes, J.; Levif, G. Tetrahedron. 1988, 44, 5263.
9. See for leading references : Ferroud, D.; Genêt, J.P.; Kiolle, R. Tetrahedron Lett.. 1986, 27, 23. Genêt, J.P.; Ferroud, D.; Montes, J.R. Ibid., 1986, 27, 4573. Genêt, J.P; Juge, S.; Mallart, S.; Ruiz Montes, J.; Levif, G. Tetrahedron. 1988, 44, 5263.
10. Nucleophiles add readily to α,β-unsaturated phosphonates, see : Minami, T.; Motoyoshiya, J. Synthesis, 1992, 333 and references cited therein.
11. 3, 40 MHz): 13.37.
12. Bäckvall, J.E.; Vagberg, J.O.; Zercher, C.; Genêt, J.P.; Denis, A. J. Org. Chem., 1987, 52, 5430.
13. 4and were used as such.
14. 3, 40 MHz): 17.48.
15. Sulsky, R.; Magnin, D.R. Synlett, 1993, 933.
16. 6 was prepared by acetylation of the corresponding α-hydroxy phosphonate, which in turn was obtained from diethyl phosphite and crotonaldehyde, see : Villemin, D.; Racha, R. Tetrahedron Lett.. 1986, 27, 1789 and Öhler, E.; Zbiral, E. Chem. Ber., 1991, 124, 175. α-Acetoxy allyl phosphonates have been used in palladium(0)-catalyzed nucleophilic substitution with amines as well as stabilized carbon nucleophiles: Zhu, J.; Lu, X. J. Chem. Soc., Chem. Comm., 1987, 1318. Zhu, J.; Lu, X. Tetrahedron Lett.. 1987, 28, 1897. Lu, X.; Sun, J.; Zhu, J. Heteroatom. Chem., 1992, 3, 551. Öhler, E.; Kanzler, S. Synthesis, 1995, 539. Öhler, E.; Kanzler, S. Phosphorus, Sulfur, Silicon and Rel. Elmts, 1996, 112, 71.
17. 6 was prepared by acetylation of the corresponding α-hydroxy phosphonate, which in turn was obtained from diethyl phosphite and crotonaldehyde, see : Villemin, D.; Racha, R. Tetrahedron Lett.. 1986, 27, 1789 and Öhler, E.; Zbiral, E. Chem. Ber., 1991, 124, 175. α-Acetoxy allyl phosphonates have been used in palladium(0)-catalyzed nucleophilic substitution with amines as well as stabilized carbon nucleophiles: Zhu, J.; Lu, X. J. Chem. Soc., Chem. Comm., 1987, 1318. Zhu, J.; Lu, X. Tetrahedron Lett.. 1987, 28, 1897. Lu, X.; Sun, J.; Zhu, J. Heteroatom. Chem., 1992, 3, 551. Öhler, E.; Kanzler, S. Synthesis, 1995, 539. Öhler, E.; Kanzler, S. Phosphorus, Sulfur, Silicon and Rel. Elmts, 1996, 112, 71.
18. 6 was prepared by acetylation of the corresponding α-hydroxy phosphonate, which in turn was obtained from diethyl phosphite and crotonaldehyde, see : Villemin, D.; Racha, R. Tetrahedron Lett.. 1986, 27, 1789 and Öhler, E.; Zbiral, E. Chem. Ber., 1991, 124, 175. α-Acetoxy allyl phosphonates have been used in palladium(0)-catalyzed nucleophilic substitution with amines as well as stabilized carbon nucleophiles: Zhu, J.; Lu, X. J. Chem. Soc., Chem. Comm., 1987, 1318. Zhu, J.; Lu, X. Tetrahedron Lett.. 1987, 28, 1897. Lu, X.; Sun, J.; Zhu, J. Heteroatom. Chem., 1992, 3, 551. Öhler, E.; Kanzler, S. Synthesis, 1995, 539. Öhler, E.; Kanzler, S. Phosphorus, Sulfur, Silicon and Rel. Elmts, 1996, 112, 71.
19. 6 was prepared by acetylation of the corresponding α-hydroxy phosphonate, which in turn was obtained from diethyl phosphite and crotonaldehyde, see : Villemin, D.; Racha, R. Tetrahedron Lett.. 1986, 27, 1789 and Öhler, E.; Zbiral, E. Chem. Ber., 1991, 124, 175. α-Acetoxy allyl phosphonates have been used in palladium(0)-catalyzed nucleophilic substitution with amines as well as stabilized carbon nucleophiles: Zhu, J.; Lu, X. J. Chem. Soc., Chem. Comm., 1987, 1318. Zhu, J.; Lu, X. Tetrahedron Lett.. 1987, 28, 1897. Lu, X.; Sun, J.; Zhu, J. Heteroatom. Chem., 1992, 3, 551. Öhler, E.; Kanzler, S. Synthesis, 1995, 539. Öhler, E.; Kanzler, S. Phosphorus, Sulfur, Silicon and Rel. Elmts, 1996, 112, 71.
20. 6 was prepared by acetylation of the corresponding α-hydroxy phosphonate, which in turn was obtained from diethyl phosphite and crotonaldehyde, see : Villemin, D.; Racha, R. Tetrahedron Lett.. 1986, 27, 1789 and Öhler, E.; Zbiral, E. Chem. Ber., 1991, 124, 175. α-Acetoxy allyl phosphonates have been used in palladium(0)-catalyzed nucleophilic substitution with amines as well as stabilized carbon nucleophiles: Zhu, J.; Lu, X. J. Chem. Soc., Chem. Comm., 1987, 1318. Zhu, J.; Lu, X. Tetrahedron Lett.. 1987, 28, 1897. Lu, X.; Sun, J.; Zhu, J. Heteroatom. Chem., 1992, 3, 551. Öhler, E.; Kanzler, S. Synthesis, 1995, 539. Öhler, E.; Kanzler, S. Phosphorus, Sulfur, Silicon and Rel. Elmts, 1996, 112, 71.
21. 6 was prepared by acetylation of the corresponding α-hydroxy phosphonate, which in turn was obtained from diethyl phosphite and crotonaldehyde, see : Villemin, D.; Racha, R. Tetrahedron Lett.. 1986, 27, 1789 and Öhler, E.; Zbiral, E. Chem. Ber., 1991, 124, 175. α-Acetoxy allyl phosphonates have been used in palladium(0)-catalyzed nucleophilic substitution with amines as well as stabilized carbon nucleophiles: Zhu, J.; Lu, X. J. Chem. Soc., Chem. Comm., 1987, 1318. Zhu, J.; Lu, X. Tetrahedron Lett.. 1987, 28, 1897. Lu, X.; Sun, J.; Zhu, J. Heteroatom. Chem., 1992, 3, 551. Öhler, E.; Kanzler, S. Synthesis, 1995, 539. Öhler, E.; Kanzler, S. Phosphorus, Sulfur, Silicon and Rel. Elmts, 1996, 112, 71.
22. 6 was prepared by acetylation of the corresponding α-hydroxy phosphonate, which in turn was obtained from diethyl phosphite and crotonaldehyde, see : Villemin, D.; Racha, R. Tetrahedron Lett.. 1986, 27, 1789 and Öhler, E.; Zbiral, E. Chem. Ber., 1991, 124, 175. α-Acetoxy allyl phosphonates have been used in palladium(0)-catalyzed nucleophilic substitution with amines as well as stabilized carbon nucleophiles: Zhu, J.; Lu, X. J. Chem. Soc., Chem. Comm., 1987, 1318. Zhu, J.; Lu, X. Tetrahedron Lett.. 1987, 28, 1897. Lu, X.; Sun, J.; Zhu, J. Heteroatom. Chem., 1992, 3, 551. Öhler, E.; Kanzler, S. Synthesis, 1995, 539. Öhler, E.; Kanzler, S. Phosphorus, Sulfur, Silicon and Rel. Elmts, 1996, 112, 71.
23. Genêt, J.P.; Juge, S.; Ruiz Montes, J.; Gaudin, J.M. J. Chem. Soc., Chem. Comm., 1988, 718. Genêt, J.P.; Kopola, N.; Juge, S.; Ruiz Montes, J.; Antunes O.A.C.; Tanier, S. Tetrahedron Lett., 1990, 31, 3133.
24. Genêt, J.P.; Juge, S.; Ruiz Montes, J.; Gaudin, J.M. J. Chem. Soc., Chem. Comm., 1988, 718. Genêt, J.P.; Kopola, N.; Juge, S.; Ruiz Montes, J.; Antunes O.A.C.; Tanier, S. Tetrahedron Lett., 1990, 31, 3133.