Conjugate additions of 1-propenylphosphonates to metalated Schollkopf's bis-lactim ether: Stereocontrolled access to 2-amino-3-methyl-4- phosphonobutanoic acids

Journal of Organic Chemistry

Volumn 65, Issue 7, 2000, Pages 1984-1995

  Ojea, Vicente ^a,b   Ruiz, María ^a,b   Shapiro, Gideon ^a   Pombo Villar, Esteban ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID DERIVATIVE; CHELATE; ETHER DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CONJUGATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

AMINOBUTYRIC ACIDS; CHEMISTRY, PHYSICAL; ETHERS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOPHOSPHORUS COMPOUNDS; RECEPTORS, METABOTROPIC GLUTAMATE; STEREOISOMERISM;

EID: 0034616359     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991402w     Document Type: Article

References (62)

1. CNS Neurotransmitters and Neuromodulators: Glutamate; Stone, T. W., Ed.; CRC: Boca Raton, FL, 1995.
2. (a) Knöpfel, T.; Gasparini, F. Drug Discovery Today 1996, 1, 103.
3. (b) Knöpfel, T.; Kuhn, R.; Allgeier, H. J. Med. Chem. 1995, 38, 1417.
4. Jane, D. E.; Pittaway, K.; Sunter, D. C.; Thomas, N. K.; Watkins, J. C. Neuropharmacology 1995, 34, 851.
5. (b) Jane, D. E.; Jones, P. L. St. J.; Pook, P. C.-K.; Tse, H.-W.; Watkins, J. C. Br. J. Pharmacol. 1994, 112, 809.
6. Ojea, V.; Conde, S.; Ruiz, M.; Fernández, M. C.; Quintela, J. M. Tetrahedron Lett. 1997, 38, 4311 and references therein.
7. Part of this work was already presented as preliminary communications: (a) Ojea, V.; Ruiz, M.; Vilar, J.; Quintela, J. M. Tetrahedron: Asymmetry 1996, 7, 3335. (b) Ojea, V.; Ruiz, M.; Shapiro, G.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 3273.
8. Part of this work was already presented as preliminary communications: (a) Ojea, V.; Ruiz, M.; Vilar, J.; Quintela, J. M. Tetrahedron: Asymmetry 1996, 7, 3335. (b) Ojea, V.; Ruiz, M.; Shapiro, G.; Pombo-Villar, E. Tetrahedron Lett. 1994, 35, 3273.
9. Perlmutter, P. In Conjugate Addition Reactions in Organic Synthesis; Baldwin, J. E., Magnus, P. D., Eds.; Organic Chemistry Series, Vol. 9; Pergamon: Oxford, 1992.
10. (a) Afarinkia, K.; Binch, H. M.; Modi, C. Tetrahedron Lett. 1998, 39, 7419.
11. (b) Baldwin, I. C.; Beckett, R. P.; Williams, J. M. J. Synthesis 1996, 34.
12. (c) Zindel, J.; Meijere, A. Synthesis 1994, 190.
13. (d) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333 and references therein.
14. (e) Darling, S. D.; Muralidharan, F. N.; Muralidharan, V. B. Tetrahedron Lett. 1979, 30, 2757 and 2761. See also references cited in ref 5b.
15. (a) Enders, D.; Wahl, H.; Papadopoulos, K. Tetrahedron 1997, 53, 12961 and references therein.
16. (b) Groth, U.; Richter, L.; Schöllkopf, U. Tetrahedron 1992, 48, 117.
17. (c) Bodalski, R.; Michalski, T.; Monkiewicz, J.; Pietrusiewicz, K. Addition of Lithium Dialkylcuprates to α,β-Unsaturated Phosphoryl Compounds. In Phosphorus Chemistry; Comstock, M. J., Ed.; ACS Symposium Series 171; American Chemical Society: Washington, DC, 1981; p 245.
18. (a) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Organic Chemistry Series, Vol. 7; Pergamon: Oxford, 1989.
19. (b) Schöllkopf, U.; Pettig, D.; Schulze, E.; Klinge, M.; Egert, E.; Benecke, B.; Noltemeyer, M. Angew. Chem., Int. Ed. Engl. 1988, 27, 1194.
20. (c) Pettig, D.; Schöllkopf, U. Synthesis 1988, 173.
21. (d) Schöllkopf, U.; Schröder, J. Liebigs Ann. Chem. 1988, 87.
22. (e) Schöllkopf, U.; Kühnle, W.; Egert, E.; Dyrbusch, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 480.
23. (f) Hartwig, W.; Born, L. J. Org. Chem. 1987, 52, 4352.
24. (g) Schöllkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Synthesis 1986, 737.
25. Ford-Moore, A. H.; Howarth Williams, J. J. Chem. Soc. 1947, 1465.
26. Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
27. (a) Ruiz, M.; Ojea, V.; Quintela, J. M. Synlett 1999, 204.
28. (b) Ruiz, M.; Ruanova, T. M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1999, 40, 2021.
29. (c) Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908.
30. (a) Schöllkopf, U.; Bardenhagen, J. Liebigs Ann. Chem. 1987, 393.
31. (b) Grauert, M.; Schöllkopf, U. Liebigs Ann. Chem. 1985, 1817.
32. Hünig, S.; Klaunzer, N.; Wenner, H. Chem. Ber. 1994, 127, 165.
33. Shapiro, G.; Buechler, D.; Ojea, V.; Pombo-Villar, E.; Ruiz, M.; Weber, H. P. Tetrahedron Lett. 1993, 34, 6255.
34. Multigram quantities of Schöllkopf's reagents were obtained from Novartis kilo laboratory.
35. (a) Berkowitz, D. B.; Eggen, M.-J.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666.
36. (b) Bergesen, K.; Vikane, T. Acta Chem. Scand. 1972, 26, 1794. For the conformational preferences of other substituted 1,2-oxaphosphorinanes, see: Tasz, M. K.; Rodriguez, O. P.; Cremer, S. E.; Hussain, M. S.; Mazhar-ul-Haque J. Chem. Soc., Perkin Trans. 2 1996, 2221, and references therein.
37. (b) Bergesen, K.; Vikane, T. Acta Chem. Scand. 1972, 26, 1794. For the conformational preferences of other substituted 1,2-oxaphosphorinanes, see: Tasz, M. K.; Rodriguez, O. P.; Cremer, S. E.; Hussain, M. S.; Mazhar-ul-Haque J. Chem. Soc., Perkin Trans. 2 1996, 2221, and references therein.
38. (a) Thatcher, G. R. J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99.
39. (b) Hall, C. R.; Inch, T. D. Tetrahedron 1980, 36, 2059.
40. Griesinger, C.; Ernst, R. R. J. Magn. Reson. 1987, 75, 261.
41. Ojea, V.; Fernández, M. C.; Ruiz, M.; Quintela, J. M. Tetrahedron Lett. 1996, 37, 5801.
42. For a review of the stereochemistry of the Michael addition reaction, see: (a) Leonard, J. Contemp. Org. Synth. 1994, 1, 387. (b) Oare, D. A.; Heathcock, C. H. Top. Stereochem. 1989, 19, 227.
43. For a review of the stereochemistry of the Michael addition reaction, see: (a) Leonard, J. Contemp. Org. Synth. 1994, 1, 387. (b) Oare, D. A.; Heathcock, C. H. Top. Stereochem. 1989, 19, 227.
44. Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathkock, C. H. J. Org. Chem. 1990, 55, 133 and references therein.
45. (a) Bernardi, A. Gazz. Chim. Ital. 1995, 125, 539.
46. (b) Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029.
47. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, and 221. Lithium PM3 parameters: Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301.
48. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, and 221. Lithium PM3 parameters: Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301.
49. Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799.
50. Stewart, J. J. P. Semiempirical Molecular Orbital Methods. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York 1990; Vol. 1, p 45.
51. (a) Hilmersson, G.; Arvidsson, P. I.; Davidsson, O.; Hakansson, M. J. Am. Chem. Soc. 1998, 120, 8143.
52. (b) Koch, R.; Wiedel, B.; Anders, E. J. Org. Chem. 1996, 61, 2523.
53. (c) Koch, R.; Anders, E. J. Org. Chem. 1995, 60, 5861.
54. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853.
55. Bauer, W.; Seebach, D. Helv. Chim. Acta 1984, 67, 1972.
56. A compact approach was also proposed in other conjugate additions: (a) Cavé, C.; Desmaële, D.; d'Angelo, J.; Riche, C.; Chiaroni, A. J. Org. Chem. 1996, 61, 4361. (b) Sevin, A.; Tortajada, J.; Pfau, M. J. Org. Chem. 1986, 51, 2671.
57. A compact approach was also proposed in other conjugate additions: (a) Cavé, C.; Desmaële, D.; d'Angelo, J.; Riche, C.; Chiaroni, A. J. Org. Chem. 1996, 61, 4361. (b) Sevin, A.; Tortajada, J.; Pfau, M. J. Org. Chem. 1986, 51, 2671.
58. Opitz, A.; Koch, R.; Katritzky, A. R.; Fan, W.-Q.; Anders, E. J. Org. Chem. 1995, 60, 3743.
59. Revised version of MOPAC93, Fujitsu Ltd, Tokyo, Japan 1993.
60. CS Chem3D Pro, version 4.0; Molecular Modeling and Analysis Program; CambridgeSoft Corporation: Cambridge, MA 02139, 1997.
61. Carvajal, C.; Tölle, K. J.; Smid, J.; Szwarc, M. J. Am. Chem. Soc. 1965, 87, 5548.
62. Pombo-Villar, E.; Boelsterli, J.; Cid, M. M.; France, J.; Fuchs, B.; Walkinshaw, M.; Weber, H.-P. Helv. Chim. Acta 1993, 76, 1203 and pertinent references therein.