Asymmetric Synthesis of Quaternary α-Amino Phosphonates Using Sulfinimines

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1757-1760

  Davis, Franklin A ^a   Lee, Seung ^a   Yan, Hongxing ^a   Titus, Donald D ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IMINE; ORGANOPHOSPHORUS COMPOUND; SULFINIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; IMINES; INDICATORS AND REAGENTS; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM; SULFINIC ACIDS;

EID: 0035979053     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015945f     Document Type: Article

References (44)

1. For a review on the biological activity of amino phosphonic acids, see: Kafarski P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193.
2. Smith, A. B., III; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879.
3. Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. J. Med. Chem. 1989, 32, 1652.
4. (a) Ding, J.; Fraser, M. E.; Meyer, J. H.; Bartlett, P. A.; James, M. N. G. J. Am. Chem. Soc. 1998, 120, 4610.
5. (b) Smith, W. W.; Bartlett, P. A. J. Am. Chem. Soc. 1998, 120, 4622 and references therein.
6. Bird, J.; Mello, R. C. D.; Harper, G. P.; Hunter, D. J.; Karran, E. H.; Markwell, R. E.; Miles-Williams, A. J.; Rahman, S. S.; Ward, R. W. J. Med. Chem. 1994, 37, 158.
7. Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengler, P. A.; Benkovic, S. J. Science 1994, 265, 234.
8. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hasssal, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S. Nature 1978, 272, 56.
9. Atherton, F. R.; Hassall, C. H.; Lambert, R. W. J. Med. Chem. 1986, 29, 29.
10. (a) Camp, N. P.; Hawkins, P. C. D.; Hitchcock, P. B.; Gani, D. Bioorg. Med. Chem. Lett. 1992, 2, 1047.
11. (b) Haebich, D.; Hansen, J.; Paessens, A. Eur. Pat. Appl. EP 472077, 1992, Bayer AG; Chem. Abstr. 1992, 117, 27161z.
12. (c) Powers, J. C.; Boduszek, B.; Oleksyszyn, J. PCT Int. Appl. WO 95 29691, 1995, Georgia Technology Research Corp.; Chem. Abstr. 1996, 124, 203102m.
13. (d) Alonso, E.; Alonso, E.; Solis, A.; del Pozo, C. Synlett 2000, 698.
14. Maier, L. Phosphorus, Sulfur Silicon 1990, 53, 43.
15. For reviews see: (a) Dhawan B.; Redmore, D. Phosphorus, Sulfur Silicon Relat. Elem. 1987, 32, 119.
16. (b) Kukhar, V. P.; Soloshonok, V. A.; Solodenko, V. A. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 92, 239.
17. (c) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279.
18. Studer, A.; Seebach, D. Heterocycles 1995, 40, 357.
19. Davis, F. A.; McCoull, W.; Titus, D. D. Org. Lett. 1999, 1, 1053.
20. Sawamura, M.; Hamashima, H.; Ito, Y. Bull. Chem. Soc. Jpn. 2000, 73, 2559.
21. Kuwano, R.; Nishio, R.; Ito, Y. Org. Lett. 1999, 1, 839.
22. The chiral HPLC separation of (+)-1-(amino-1-phenylethyl)phosphonic acid (41%) has been reported; see: Zarbl, E.; Lammerhofer, M.; Hammerschmidt, F.; Wuggenig, F.; Hanbauer, M.; Maier, N. M.; Sajovic, L.; Lindner, W. Anal. Chim. Acta 2000, 404, 169.
23. For leading references, see: Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 65, 8704.
24. (a) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
25. (b) Fanelli, D. L.; Szewczyk, J. M.; Zhang, Y.; Reddy, G. V.; Burns, D. M.; Davis, F. A. Org. Synth. 1999, 77, 50.
26. Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J. Tetrahedron: Asymmetry 1997, 8, 3991.
27. For reviews on the chemistry of sulfinimines, see: (a) Zhou, P.; Chen, B.-C.; Davis, F. A. Syntheses and Reactions of Sulfinimines. In Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press: Stamford, CT, 2000; Vol 2; pp 249-282.
28. (b) Hua, D. H.; Chen, Y.; Millward, G. S. Sulfur Reports 1999, 21, 211.
29. Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
30. Davis, F. A.; Andemichael, Y. W. J. Org. Chem. 1999, 64, 8627 and references therein.
31. Davis, F. A.; Mohanty, P. K.; Burns, D. M.; Andemichael, Y. W. Org. Lett. 2000, 2, 3901.
32. Chan, W. H.; Lee, A. W. M.; Xia, P. F.; Wong, W. Y. Tetrahedron Lett. 2000, 41, 5725.
33. (a) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396.
34. (b) Bravo, P.; Crucianelli, M.; Vergani, B.; Zanda, M. Tetrahedron Lett. 1998, 39, 7771.
35. Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J.; Wieczorek, M. W.; Blaszczyk, J. Chem. Commun. 1996, 1503.
36. (a) Davis, F. A.; McCoull, W., Titus, D. D. Org. Lett. 1999, 1, 1053.
37. (b) Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249.
38. Viso, A.; de la Pradilla, R. F.; Guerrero-Strachan, C.; Alonso, M.; Martinez-Ripoll, M.; Andre, I. J. Org. Chem. 1997, 62, 2316.
39. Viso, A.; de la Pradilla, R. F.; Garcia, A.; Alonso, M.; Guerrero-Strachan, C.; Fonseca, I. Synlett 1999, 1543.
40. Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532.
41. The absolute configuration of (R)-(+)-α-amino (phenylmethyl)-phosphoninc acid (12) was established by X-ray crystallography: Glowiak, T.; Sawka-Dobrowolski, W.; Kowalik, J.; Mastalerz, P.; Soroka, M.; Zon, J. Tetrahedron Lett. 1977, 3965.
42. Upon re-analysis Smith et al. have confirmed that the configuration assigned to the phospho-phenylglycine derivatives (+)-12 is indeed R. Ambiguous representation of the C1 (α carbon) stereochemistry reported by Soroka and co-workers (ref 30) allowed this error to go previously undetected.
43. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
44. For a discussion of the conformations of cycloheptanes, see: Bocian, D. F.; Pickett, H. M.; Rounds, T. C.; Strauss, H. L. J. Am. Chem. Soc. 1975, 97, 687.