Synthesis of (1S,2S)- and (1R,2R)-1-amino-2-methylcyclopropane-phosphonic acids from racemic methylcyclopropanone acetal

Tetrahedron Asymmetry

Volumn 13, Issue 20, 2002, Pages 2267-2276

  Tesson, Nicolas ^a   Dorigneux, Benoist ^a   Fadel, Antoine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; PHOSPHINIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROGENOLYSIS; HYDROLYSIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0037131662     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00609-2     Document Type: Article

References (25)

1. For some recent reviews, see: (a) Stammer, C. Tetrahedron 1990, 46, 2231-2254; (b) Alami, A.; Calmes, M.; Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5-24.
2. For some recent reviews, see: (a) Stammer, C. Tetrahedron 1990, 46, 2231-2254; (b) Alami, A.; Calmes, M.; Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5-24.
3. Burgess K., Kwok-Kan H., Destradi M.S. Synlett. 1994;575-583.
4. Jimenez J.M., Rife J., Ortuño R.M. Tetrahedron: Asymmetry. 7:1996;537-558.
5. For a comprehensive review, see: Dhawan B., Redmore D. Phosphorus Sulfur Relat. Elem. 32:1987;119-144.
6. Kafarski B., Lejczak B. Phosphorus Sulfur Silicon. 63:1991;193-215.
7. De Lombaert S., Blanchard L., Tan J., Sakane Y., Berry C., Ghai R.D. Bioorg. Med. Chem. Lett. 5:1995;145-150.
8. Atherton F.R., Hassall C.H., Lambert R.W. J. Med. Chem. 29:1986;29-40. and references cited therein.
9. Wolfenden, R. Annu. Rev. Biophys. Bioeng. 1976, 5, 271-306; Chem. Abstr. 1976, 85, 73952b.
10. Wolfenden, R. Annu. Rev. Biophys. Bioeng. 1976, 5, 271-306; Chem. Abstr. 1976, 85, 73952b.
11. Jacobsen N.E., Bartlett P.A. J. Am. Chem. Soc. 103:1981;654-657.
12. For a synthesis of racemic substituted α-aminocyclopropanephosphonic acid, see: Groth U., Lehmann L., Richter L., Schöllkopf U. Liebigs Ann. Chem. 1993;427-431.
13. For an optically active synthesis, see: (a) Yamazaki, S.; Takoda, T.; Moriguchi, Y.; Yamabe, S. J. Org. Chem. 1998, 63, 5919-5928; (b) Hercouet, A.; Le Corre, M.; Carboni, B. Tetrahedron Lett. 2000, 41, 197-199.
14. For an optically active synthesis, see: (a) Yamazaki, S.; Takoda, T.; Moriguchi, Y.; Yamabe, S. J. Org. Chem. 1998, 63, 5919-5928; (b) Hercouet, A.; Le Corre, M.; Carboni, B. Tetrahedron Lett. 2000, 41, 197-199.
15. Fadel A. J. Org. Chem. 64:1999;4953-4955.
16. Fadel A. Synlett. 1993;503-505.
17. Fadel A., Khesrani A. Tetrahedron: Asymmetry. 9:1998;305-320. and references cited therein.
18. Fadel A., Tesson N. Eur. J. Org. Chem. 2000;2153-2159.
19. Fadel A., Tesson N. Tetrahedron: Asymmetry. 11:2000;2023-2031.
20. Volk F.-J., Frahm A.W. Liebigs Ann. 1996;1893.
21. Edwards R. J. Am. Chem. Soc. 64:1942;1583.
22. Vachal P., Jacobsen E.N. Org Lett. 2:2000;867.
23. Losse D., Nadolski D. J. Prakt. Chem. 24:1964;118.
24. Mosher H.S., Dale J.A., Dull D.L. J. Org. Chem. 34:1969;2543-2549.
25. Part of Tesson, N., Ph.D. Thesis, Université Paris-Sud, Orsay, France, 16 November 2001.