Asymmetric synthesis of a phosphonic analogue of (-)-allo-norcoronamic acid

Tetrahedron Letters

Volumn 41, Issue 2, 2000, Pages 197-199

  Hercouet, Alain ^a   Le Corre, Maurice ^a   Carboni, Bertrand ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Amino phosphonic acid; Asymmetric synthesis; Cyclic sulfates; Cyclopropane

Indexed keywords

CYCLOPROPANE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID; SULFATE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034620191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02036-5     Document Type: Article

References (15)

1. For some recent reviews, see: (a) Stammer, C. H. Tetrahedron 1990, 46, 2231-2254. (b) Alami, A.; Calmes, M.; Daunis, J.; Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5-24. (c) Burgess, K.; Kwok-Kan, H.; Destradi, M. S. Synlett 1994, 575-583.
2. For some recent reviews, see: (a) Stammer, C. H. Tetrahedron 1990, 46, 2231-2254. (b) Alami, A.; Calmes, M.; Daunis, J.; Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5-24. (c) Burgess, K.; Kwok-Kan, H.; Destradi, M. S. Synlett 1994, 575-583.
3. For some recent reviews, see: (a) Stammer, C. H. Tetrahedron 1990, 46, 2231-2254. (b) Alami, A.; Calmes, M.; Daunis, J.; Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5-24. (c) Burgess, K.; Kwok-Kan, H.; Destradi, M. S. Synlett 1994, 575-583.
4. Hiratake, J.; Oda, J. Biosci., Biotechnol., Biochem. 1997, 61, 211-218.
5. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 283-284. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 1267-1268. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron Lett. 1996, 37, 4529-4531. Hercouet, A.; Godbert, N.; Le Corre, M. Tetrahedron: Asymmetry 1998, 9, 2233-2234.
6. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 283-284. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 1267-1268. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron Lett. 1996, 37, 4529-4531. Hercouet, A.; Godbert, N.; Le Corre, M. Tetrahedron: Asymmetry 1998, 9, 2233-2234.
7. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 283-284. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 1267-1268. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron Lett. 1996, 37, 4529-4531. Hercouet, A.; Godbert, N.; Le Corre, M. Tetrahedron: Asymmetry 1998, 9, 2233-2234.
8. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 283-284. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron: Asymmetry 1996, 7, 1267-1268. Hercouet, A.; Bessières, B.; Le Corre, M. Tetrahedron Lett. 1996, 37, 4529-4531. Hercouet, A.; Godbert, N.; Le Corre, M. Tetrahedron: Asymmetry 1998, 9, 2233-2234.
9. Cativiela, C.; Diaz-de-Villegas, M. D.; Jiménez, A. I. Tetrahedron: Asymmetry 1995, 6, 177-182.
10. For a synthesis of the racemic 1-amino-2-methylcyclopropanephosphonic acid, see: Groth, U.; Lehmann, L.; Richer, L.; Schöllkopf, U. Liebigs Ann. Chem. 1993, 427-431.
11. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538-7539.
12. +) 264.1126.
13. 31P NMR spectrum of a diastereomeric mixture of cyclopropanes 4, obtained from the racemic sulfate 2, displayed four signals at 30.50, 30.61, 31.78, and 31.85 ppm in a 1.5, 1.5, 48.5, 48.5 ratio. These results were not dependent on the reaction time of salt formation, that excludes a kinetic resolution.
14. 2O) δ 16.93.
15. -1, T=294 K, F(000)=176, R=0.105 for 1836 reflections.