Asymmetric synthesis of (R)- and (S)-piperidin-2-yl-phosphonic acid by diastereoselective addition of trialkyl phosphite onto potential iminium salt

Tetrahedron

Volumn 53, Issue 10, 1997, Pages 3627-3636

  Maury, Catherine ^a   Wang, Qian ^a   Gharbaoui, Tawfik ^a   Chiadmi, Mohamed ^b   Tomas, Alain ^b   Royer, Jacques ^a   Husson, Henri Philippe ^a,b  

^a CNRS   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562429     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00086-0     Document Type: Article

References (17)

1. 1) For recent asymmetric syntheses see: a) Smith, A. B.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879-10888.
2. b) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656-6657.
3. c) Hamilton, R.; Walker, B; Walker, B. J. Tetrahedron Lett. 1995, 36, 4451-4454.
4. d) Cabella, G.; Jommi, G.; Pagliarin, R.; Sello, G.; Sisti, M. Tetrahedron 1995, 51, 1817-1826.
5. e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687-3693 and references cited therein,
6. f) Gröger, H.; Saida, Y.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291-9292
7. 2) a) Guerrier, L.; Royer, J.; Grierson, D.S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
8. b) Bonin, M. Grierson, D.S.; Royer, J.; Husson, H.-P. Org. Syntheses, 1992, 70, 54-59.
9. c) Royer, J.; Husson, H.-P. in "Advances in the Use of Synthons in Organic Chemistry", Dondoni, A. Ed., Jai Press Inc. 1995, vol 2, p 1-68
10. 3) Jacquier, R.; Ouazzani, F.; Roumestan, M.-L.; Viallefont, P. Phosphorus and Sulfur, 1988, 36, 73-77.
11. 4) a) Bergesen, K. Acta Chim. Scand. 1967, 21, 578-579.
12. b) Bergesen, K.; Vikane, T. Acta Chim. Scand. 1972, 26, 1794-1795.
13. 5) Majoral, J.-P.; Navech, J. Bull. Soc. Chim. France 1971, 95-98
14. b) Majoral, J.-P.; Bergounhou, C.; Navech, J. Bull. Soc. Chim. France 1973, 3146-3149
15. c) Majoral, J.-P.; Bergounhou, C.; Navech, J.; Maria, P.C.; Elegant, L.; Azzaro, M. Bull. Soc. Chim. France 1973, 3142-3145
16. 6) Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Göttingen, Germany.
17. 7) Sheldrick, G.M. (1976). SHELX76. Program for crystal structure determination. Univ. of Cambridge, England.