Rapid and efficient access to meso-2,5-cis-disubstituted pyrrolidines by double aza-Michael reactions of chiral primary amines

Heterocycles

Volumn 73, Issue C, 2007, Pages 751-768

  Cabral dos Santos, Leila ^a,b   Bahlaouan, Zineb ^a,b   El Kassimi, Khadija ^a,b   Troufflard, Claire ^a,b   Hendra, Frédéric ^a,b   Delarue Cochin, Sandrine ^a,b   Zahouily, Mohamed ^c   Cavé, Christian ^a,b   Joseph, Delphine ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b IPSIT   (France)

^c HASSAN II UNIVERSITY OF CASABLANCA   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 45149087440     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-07-S(U)56     Document Type: Article

References (29)

1. Pichon M., and Figadère B. Tetrahedron: Asymmetry 7 (1996) 927
2. Daley V., d'Angelo J., Cavé C., Mahuteau J., Chiaroni A., and Riche C. Tetrahedron Lett. 40 (1999) 1657
3. Davies S.G., Smith A.D., and Price P.D. Tetrahedron: Asymmetry 16 (2005) 2833 and references cited therein
4. Urones J.G., Garrido N.M., Diez D., Dominguez S.H., and Davies S.G. Tetrahedron: Asymmetry 8 (1997) 2683
5. Urones J.G., Garrido N.M., Diez D., Dominguez S.H., and Davies S.G. Tetrahedron: Asymmetry 10 (1999) 1637
6. Urones J.G., Garrido N.M., Diez D., El Hammoumi H., Dominguez S.H., Casaseca J.A., Davies S.G., and Smith A.D. Org. Biomol. Chem. 2 (2004) 364
7. Garrido N.M., El Hammoumi M.M., Diez D., and Urones J.G. Molecules 9 (2004) 373
8. Rulev A.Y., Yenil N., Pesquet A., Oulyadi H., and Maddaluno J. Tetrahedron 62 (2006) 5411
9. Bargiggia F.C., and Murray W.V. Tetrahedron Lett. 47 (2006) 3191
10. Lang R.W., and Hansen H.-J. Org. Synth. 7 (1990) 232
11. Enders D., and Schü T. Synthesis (2002) 2280
12. House H.O., and Cronin T.H. J. Org. Chem. 30 (1965) 1061
13. Williams J.R. J. Chem. Sot., Chem. Commun. (1981) 752
14. Klimko P.G., and Singleton D.A. J. Org. Chem. 57 (1992) 1733
15. (R)-Phenylglycinol was prepared according to the Masamune's procedure by reduction of (R)-phenylglycine. Abiko A., and Masamune S. Tetrahedron Lett. 33 (1992) 5517
16. Dumas F., Mezrhab B., and d'Angelo J. J. Org. Chem. 61 (1996) 2293
17. Yeom C.-E., Kim M.J., and Kim B.M. Tetrahedron 63 (2007) 904
18. Zahouily M., Bahlaouan B., Rayadh A., and Sebti S. Tetrahedron Lett. 45 (2004) 4135 and references cited therein
19. Camara C., Keller L., Jean-Charles K., Joseph D., and Dumas F. High Press. Res. 24 (2004) 149
20. d'Angelo J., and Maddaluno J. J. Am. Chem. Soc. 108 (1986) 8112
21. Dumas F., Mezrhab B., d'Angelo J., Riche C., and Chiaroni A. J. Org. Chem. 61 (1996) 2293
22. Jenner G. NewJ. Chem. 19 (1995) 173
23. K. Jean-Charles and F. Dumas, unpublished results.
24. Abrouki Y., Zahouily M., Rayadh A., Bahlaouan B., and Sebti S. Tetrahedron Lett. 43 (2002) 8951
25. Werkhoven T.M., van Nispen R., and Lugtenburg J. Eur. J. Org. Chem. (1999) 2909
26. Aitken R.A., Armstrong J.M., Drysdale M.J., Ross F.C., and Ryan B.M. J. Chem. Soc., Perkin Trans 1 (1999) 593
27. Klimko P.G., and Singleton D.A. J. Org. Chem. 57 (1992) 1733
28. Harusawa S., Shibata N., Yamazaki N., Sakanoue S., Ishida T., Yoneda R., and Kurihara T. Chem. Pharm. Bull. 37 (1989) 2647
29. -1) 1714 (C=O), 2839, 2734 (CH).