Stereo- And enantioselective synthesis of acetylenic 2-amino-1,3-diol stereotriads

Organic Letters

Volumn 11, Issue 4, 2009, Pages 931-934

  Voituriez, Arnaud ^a   Pérez Luna, Alejandro ^a   Ferreira, Franck ^a   Botuha, Candice ^a   Chemla, Fabrice ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AMINE; IMINE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AMINES; IMINES; MOLECULAR STRUCTURE; STEREOISOMERISM; ZINC;

EID: 62749196628     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802912f     Document Type: Article

References (44)

1. (1) (a) Michael, J. P. Nat. Prod. Re 2008, 25, 139.
2. (b) Ayad, T.; Genisson, Y.; Baltas, M. Curr. Org. Chem. 2004, 8, 1211.
3. (2) Botuha, C.; Chemla, F.; Ferreira, F.; Pérez-Luna, A.; Roy, B. New J. Chem. 2007, 31, 1552.
4. (3) (a) Palais, L.; Chemla, F.; Ferreira, F. Synlett., 2006, 1039.
5. (b) Chemla, F.; Ferreira, F.; Gaucher, X.; Palais, L. Synthesis 2007, 1235.
6. (4) (a) Bernard, N.; Chemla, F.; Normant, J. Tetrahedroron Lett. 1999, 40, 75.
7. (b) Chemla, F.; Bernard, N.; Ferreira, F.; Normant, J.-F. Eur. J. Org. Chem. 2001, 3295.
8. (c) Chemla, F.; Hebbe, V.; Normant, J.-F. Tetrahedron Lett. 1999, 40, 8093.
9. (d) Chemla, F.; Ferreira, F.; Hebbe, V.; Stercklen, E. Eur. J. Org. Chem. 2002, 1385.
10. (e) Ferreira, F.; Bejjani, J.; Denichoux, A.; Chemla, F. Synlett., 2004, 2051.
11. (5) (a) Chemla, F.; Ferreira, F. Synlett., 2004, 983.
12. (b) Chemla, F.; Ferreira, F. J. Org. Chem. 2004, 69, 8244.
13. (6) Ferreira, F.; Audouin, M.; Chemla, F. Chem.-Eur. J. 2005, 11, 5269.
14. (7) Roy, B; Pérez-Luna, A.; Ferreira, F.; Botuha, C.; Chemla, F. Tetrahedrorn Lett. 2008, 49, 1534.
15. (8) Chemla, F.; Ferreira, F. Synlett., 2006, 2613.
16. (9) Voituriez, A.; Ferreira, F.; Chemla, F. J. Org. Chem. 2007, 72, 5358.
17. (10) Voituriez, A.; Ferreira, F.; Prez-Luna, A.; Chemla, F. Org. Lett. 2007, 9, 4705.
18. (11) Hjelmgaard, T.; Faure, S.; Lemoine, P.; Viossat, B.; Aitken, D. J. Org. Lett. 2008, 10, 841.
19. (12) (a) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317.
20. (b) Weix, D. J.; Ellman, J. A. Org. Synth. 2005, 82, 157.
21. (13) Evans, J. W.; Ellman, J. A. J. Org. Chem. 2003, 68, 9948.
22. (14) Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
23. (15) See the Supporting Information.
24. (16) It is known that vicinal coupling constants in 4, 5-disubstituted oxazolidinones are higher for the cis
25. (6-8 Hz) than for the trans isomer
26. (4-6 Hz) ; see: (a) Reference 3a and:
27. (b) Foglia, T. A.; Swern, D. J. Org. Chem. 1969, 34, 1680.
28. (c) Futagawa, S.; Inui, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1973, 46, 3308.
29. (d) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Laboroi, F.; Mazzanti, G.; Ricci, A.; Varchi, G. J. Org. Chem. 1999, 64, 8008.
30. (e) Poisson, J.-F.; Chemla, F.; Normant, J. F. Synlett., 2001, 305.
31. (17) Poisson, J. F.; Normant, J.-F. Org Lett. 2001, 3, 1889.
32. (18) For a general review on chiral sulfinimines, see: (a) Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869.
33. (b) Ferreira, F.; Botuha, C.; Chemla, F.; Perez-Luna, A. Chem. Soc. Rev. 2009, DOI: 10.1039 /B809772K.
34. (19) Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883.
35. (20) (a) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
36. (b) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772.
37. (21) (a) Denolf, B.; Mangelinckx, S.; Tornoos, K. W.; De Kimpe, N. Org. Lett. 2006, 8, 3129.
38. (d) Hodgson, D. M.; Kloesges, J.; Evans, B. Org. Lett 2008, 10, 2781.
39. (22) (a) Prakash, G. K. S.; Mandal, M. J. Am. Chem. Soc. 2002, 124, 6538.
40. (b) Liu, J.; Li, Y.; Hu, J. J. Org. Chem. 2007, 72, 3119.
41. (23) (a) Denolf, B.; Leemans, E.; De Kimpe, N. J. Org. Chem. 2007, 72, 3211.
42. (b) Denolf, B.; Leemans, E.; De Kimpe, N. J. Org. Chem. 2008, 73, 5662.
43. (24) (a) Bharatam, P. V.; Uppal, P.; Amita Kaur, D. J. Chem. Soc., Perkin Trans. 2 2000, 43.
44. (b) Bharatam, P. V.; Amita Kaur, D. J. Phys. Org. Chem. 2002, 15, 197. A Convergent Approach toward the C1#C11 Subunit of Phoslactomycins and Formal Synthesis of Phoslactomycin B