An Efficient Stereocontrolled Synthesis of (R)-2-Carboxy-4-(3-phoshonopropyl)piperazine [(R)-CPP]

Synlett

Volumn 1996, Issue 2, 1996, Pages 143-144

  Falorni, Massimo ^a   Giacomelli, Giampaolo ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002523511     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5341     Document Type: Article

References (18)

1. See for examples: Johnson, R.L.; Koerner, J.F. J. Med. Chem., 1988, 31, 2057. Hashimoto, K.; Shirahama, H. Tetrahedron Lett., 1991, 32, 2625.
2. See for examples: Johnson, R.L.; Koerner, J.F. J. Med. Chem., 1988, 31, 2057. Hashimoto, K.; Shirahama, H. Tetrahedron Lett., 1991, 32, 2625.
3. Hays, S.J.; Bigge, C.F.; Novak, P.M.; Drummond, J.T.; Bobovski, T.P.; Rice, M.J.; Johnson, G.; Brahce, L.J.; Coughenour, L.L. J. Med. Chem., 1990, 33, 2916.
4. Aebisher, B.; Frey, P.; Haerter, H.-P.; Herrling, P.L.; Mueller, W.; Olverman, H.J.; Watkins, J.C. Helv. Chim. Acta , 1989, 72, 1043.
5. Bruce, M.A.; St. Laurent, D.R.; Poindexter, G.S.; Monkovic, I.; Huang, S.; Balasubramanian, N. Synth. Commun., 1995, 25, 2673.
6. Falorni, M.; Giacomelli, G.; Satta, M.; Cossu, S. Synthesis, 1994, 391. Rossen, K.; Weissman, S.A.; Sager, J.; Reamer, R.A.; Askin, D.; Volante R.P.; Reider, P.J. Tetrahedron Lett., 1995; 36, 6419.
7. Falorni, M.; Giacomelli, G.; Satta, M.; Cossu, S. Synthesis, 1994, 391. Rossen, K.; Weissman, S.A.; Sager, J.; Reamer, R.A.; Askin, D.; Volante R.P.; Reider, P.J. Tetrahedron Lett., 1995; 36, 6419.
8. 3: C, 45.57; H, 6.37; N, 17.71. Found: C, 45.48; H, 6.39; N, 17.73.
9. 6: C, 55.55; H, 6.22; N, 8.64. Found: C, 55.60; H, 6.10; N, 8.59.
10. Ueda, T.; Saito, M.; Kato, T.; Izumya, N. Bull. Chem. Soc. Jpn., 1983, 56, 568.
11. 2O: C, 55.35; H, 10.84; N, 21.52. Found: C, 55.27; H, 10.89; N, 21.51.
12. 3: C, 57.37; H, 9.63; N, 12.16. Found: C, 57.49; H, 9.59; N, 12.08.
13. Eberard, A.; Westheimer, F.H. J. Am. Chem. Soc., 1965, 87, 253.
14. 6PI: C, 40.31; H, 7.14; N, 5.22. Found: C, 40.26; H, 7.12; N, 5.29.
15. Carlsen, H.J.; Katsuki, T.; Martin, V.S.; Sharpless K.B. J. Org. Chem., 1981, 46, 3936.
16. 2O: C, 45.47; H, 8.90; N, 8.84. Found: C, 45.35; H, 8.94; N, 9.92.
17. The unique example of demethylation of quaternary ammonium salt with PhSNa was described on simple alkyl and arylamines: Shamma, M.; Deno, N.C.; Remar, J.F. Tetrahedron Lett., 1966, 1375.
18. 2O: C, 33.56; H, 6.69; N, 9.79. Found: C, 33.48; H, 6.72; N, 9.83.