N,OHighly regio- and stereoselective alkylation of nucleophilic glycine equivalents with carbonates of allylic α-hydroxyphosphonates: A convenient route to racemic 2-amino-5-phosphono-4-pentenoic acids

Liebigs Annales

Volumn , Issue 7, 1997, Pages 1437-1445

  Öhler, Elisabeth ^a   Kanzler, Silvia ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

Alkylations; Allylic alkylation, palladium(0) catalyzed; Glycine equivalents; Palladium; Phosphonate substituted allylic carbonates; Regioselectivity; Stereoselectivity

Indexed keywords

EID: 33748841330     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970722     Document Type: Article

References (59)

1. R. H. Evans, A. A. Francis, A. W. Jones, D. A. S. Smith, J. C. Watkins, Br. J. Pharmacol. 1982, 75, 65-75.
2. H. Allgeier, C. Angst, G. Bold, R. Duthaler, R. Heckendorn, A. Togni (Ciba-Geigy A.-G.), EP 302 826, 1989; [Chem. Abstr. 1990, 112, 139560g].
3. M. Kirihata, S. Kawahara, I. Ichimoto, H. Ueda, Agric. Biol. Chem. 1990, 54, 753-756;
4. [Chem. Abstr. 1990, 113, 115811j].
5. C. Angst, D. E. Brundish, J. G. Dingwall, G. E. Fagg (Ciba-Geigy A.-G.), EP 233 154, 1987; [Chem. Abstr. 1988, 109, 110903y].
6. G. E. Fagg, L. Massieu, M. Schmutz, M. F. Pozza, F. Brugger, H. R. Olpe, Fidia Res. Found. Symp. Ser. 1991, 5, 687-683;
7. Chem. Abstr. 1991, 115, 247265k.
8. H. Allgeier (Ciba-Geigy Corp.), US 5134134, 1992; [Chem. Abstr. 1993, 118, 7390r].
9. C. Angst, H. Allgeier, R. Heckendorn, D. Wallach (Ciba-Geigy Corp.), US 5294734, 1994; [Chem. Abstr. 1995, 122, 10255p].
10. B. K. Park, A. Hirota, H. Sakai, Agric. Biol. Chem. 1977, 41, 573-579.
11. [10].
12. A. Fredenhagen, C. Angst, H. H. Peter, J. Antibiot. 1995, 48, 1043-1045.
13. C. Rapp, G. June, M. Kugler, W. Loeffler, Liebigs Ann. Chem. 1988, 655-661.
14. C. Harde, K.-H. Neff, E. Nordhoff, K.-P. Gerbling, B. Laber, H.-D. Pohlenz, Bioorg. Med. Chem. Lett. 1994, 4, 273-278.
15. B. Laber, K.-P. Gerbling, C. Harde, K.-H. Neff, E. Nordhoff, H.-D. Pohlenz, Biochemistry 1994, 33, 3413-3423.
16. E. Öhler, S. Kanzler, Synthesis 1995, 539-543, and references therein.
17. E. Öhler, S. Kanzler, Phosphorus, Sulfur, Silicon 1996, 112, 71-90.
18. For a recent literature survey concerning the reactivity of allylic α-hydroxyphosphonates see: E. Öhler, S. Kanzler, Monatsh. Chem. 1996, 127, 177-183.
19. [17a] J.P. Haudegond, Y. Chauvin, D. Commereuc, J. Org. Chem. 1979, 44, 3063-3065. -
20. [17b] L. V. Dunkerton, A. J. Serino, J. Org. Chem. 1982, 47, 2812-2814. -
21. [17c] N. Kopola, B. Friess, B. Cazes, J. Gore, Tetrahedron Lett. 1989, 30, 3963-3966. -
22. [17d] M. Yamaguchi, T. Shima, T. Yamagishi, M. Hida, Tetrahedron Lett. 1990, 31, 5049-5052. -
23. [17e] M. Yamaguchi, T. Shima, T. Yamagishi, M. Hida, Tetrahedron: Asymmetry 1991, 2, 663-666.
24. [18a] J. P. Genet, D. Ferroud, S. Juge, J. R. Montes, Tetrahedron Lett. 1986, 27, 4573-4576. -
25. [18b] B. Cazes, D. Djahanbini, J. Gore, J. P. Genet, J. M. Gaudin, Synthesis 1988, 983-985. -
26. [18c] J. P. Genet, S. Juge, I. Besnier, J. Uziel, D. Ferroud, N. Kardos, S. Achi, J. Ruiz-Montes, S. Thorimbert, Bull. Soc. Chim. Fr. 1990, 127, 781-786. -
27. [18d] J. P. Genet, N. Kopola, S. Juge, J. Ruiz-Montes, O. A. C. Antunes, S. Tanier, Tetrahedron Lett. 1990, 31, 3133-3136. -
28. [18e] J. P. Genet, S. Thorimbert, S. Mallart, N. Kardos, Synthesis 1993, 321-324. -
29. [18f] I. C. Baldwin, J. M. J. Williams, Tetrahedron: Asymmetry 1995, 6, 1515-1518. -
30. [18g] A. Mazon, C. Najera, J. Ezquerra, C. Pedregal, Tetrahedron Lett. 1995, 36, 7697-7700.
31. [19a] D. Ferroud, J. P. Genet, R. Kiolle, Tetrahedron Lett. 1986, 27, 23-26. -
32. [19b] J. P. Genet, S. Juge, S. Achi, S. Mallart, J. Ruiz-Montes, G. Levif, Tetrahedron 1988, 44, 5263-5275. -
33. [19c] A. Gaucher, P. Dorizon, J. Ollivier, J. Salaün, Tetrahedron Lett. 1995, 36, 2979-2982.
34. Y. Ito, M. Sawamura, M. Matsuoka, Y. Matsumoto, T. Hayashi, Tetrahedron Lett. 1987, 28, 4849-4852.
35. J. Zhu, X. Lu, J. Chem. Soc., Chem. Commun. 1987, 1318-1319.
36. X. Lu, J. Sun, J. Zhu, Heteroatom Chem. 1992, 3, 551-557 (In this paper, there is no report on the ratio of stereoisomers obtained).
37. J. Zhu, X. Lu, Tetrahedron Lett. 1987, 28, 1897-1900.
38. The formation of allylic ethers during alkylation reactions performed with allylic carbonates can be explained by the concomitant attack of the alkoxide generated from the carbonate during formation of the π-allyl complex[25,26].
39. J. Tsuji, I. Shimizu, I, Minami, Y. Ohashi, Tetrahedron Lett. 1982, 23, 4809-4812.
40. Y. Tsuji, N. Yamada, S. Tanaka, J. Org. Chem. 1993, 58, 16-17.
41. [27a] P. M. Maitlis, P. Espinet, M. J. H. Russell in Comprehensive Organometallic Chemistry, I (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, vol. 6, p. 385-454. -
42. [27b] P. J. Harrington in Comprehensive Organometallic Chemistry, II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, vol. 12, p. 798-904.
43. The role of BSA in transition state promoted allylic alkylations has not been clearly defined. For a discussion of this problem and leading references see: R. Sulsky, D. R. Magnin, Synlett 1993, 933-934.
44. [27]. For an attempt to control the (E/Z)-stereochemistry in palladium-promoted allylic substitution reactions by selective stabilization of the anti-isomer via ligand geometry see: B. Åkermark, S. Hansson, A. Vitagliano, J. Am. Chem. Soc. 1990, 112, 4587-4588.
45. [32].
46. E. Öhler, S. Kotzinger, Synthesis 1993, 497-502, and references therein.
47. J. Zindel, A. de Meijere, Synthesis 1994, 190-194.
48. C. Benezra, J. Am. Chem. Soc. 1973, 95, 6890-6894.
49. G. Grossmann, R. Lang, G. Ohms, D. Scheller, Magn. Reson. Chem. 1990, 28, 500-504, and references therein.
50. K. Matoba, H. Yonemoto, M. Fukui, T. Yamazaki, Chem. Pharm. Bull. 1984, 32, 3918-3925.
51. P. L. Ornstein, Org. Prep. Proc. Int. 1988, 20, 371-376.
52. [39], have been reported.
53. P. L. Ornstein, J. Org. Chem. 1989, 54, 2251-2253.
54. O. García-Barradas, E. Juaristi, Tetrahedron 1995, 57, 3423-3434.
55. [14,15].
56. [38], respectively, but yields were generally low, and/or purification troublesome.
57. K. Hemmi, H. Takeno, M. Hashimoto, T. Kamiya, Chem. Pharm. Bull. 1982, 30, 111-118.
58. E. Öhler, S. Kotzinger, Liebigs Ann. Chem. 1993, 269-280.
59. F. Texier-Boullet, A. Foucaud, Synthesis 1982, 165-166.