Stereospecific rearrangement of β-amino alcohols catalyzed by H 2SO4

Synlett

Volumn , Issue 18, 2007, Pages 2888-2890

  Métro, Thomas Xavier ^a   Pardo, Domingo Gomez ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

Amino alcohols; Catalysis; Chiral pool; Rearrangement; Stereoselective synthesis

Indexed keywords

AMINOALCOHOL; SULFURIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 36549067655     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992351     Document Type: Article

References (26)

1. (a) Brode, W. R.; Hill, M. W. J. Am. Chem. Soc. 1947, 69, 724.
2. (b) Back, T. G.; Parvez, M.; Zhai, H. J. Org. Chem. 2003, 68, 9389.
3. (c) Couty, F.; Durrat, F.; Prim, D. Tetrahedron Lett. 2004, 45, 3725.
4. (d) Sivaprakasam, M.; Couty, F.; Evano, G.; Srinivas, B.; Sridhar, R.; Rama Rao, K. Synlett 2006, 781.
5. Nagle, A. S.; Salvatore, R. N.; Chong, B.-D.; Jung, K. W. Tetrahedron Lett. 2000, 41, 3011.
6. (a) Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W. J. Org. Chem. 1992, 57, 1663.
7. (b) Gmeiner, P.; Junge, D.; Kaertner, A. J. Org. Chem. 1994, 59, 6766.
8. (c) Weber, K.; Kuklinski, S.; Gmeiner, P. Org. Lett. 2000, 2, 647.
9. (d) Frizzle, M. J.; Caille, S.; Marshall, T. L.; McRae, K.; Nadeau, K.; Guo, G.; Wu, S.; Martinelli, M. J.; Moniz, G. A. Org. Process Res. Dev. 2007, 11, 215.
10. Lehmann, T.; Hübner, H.; Gmeiner, P. Bioorg. Med. Chem. Lett. 2001, 11, 2863.
11. Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323.
12. Freedman, J.; Vaal, J. V.; Huber, E. W. J. Org. Chem. 1991, 56, 670.
13. McKay, C.; Wilson, R. J.; Rayner, C. M. Chem. Commun. 2004, 1080.
14. Hook, D. F.; Gessier, F.; Noti, C.; Kast, P.; Seebach, D. ChemBioChem 2004, 5, 691.
15. Ye, C.; Shreeve, J. M. J. Fluorine Chem. 2004, 125, 1869.
16. Métro, T.-X.; Appenzeller, J.; Gomez Pardo, D.; Cossy, J. Org. Lett. 2006, 8, 3509.
17. For examples of cyclic β-amino alcohols rearrangement, see: (a) Cossy, J.; Dumas, C.; Gomez Pardo, D. Eur. J. Org. Chem. 1999, 1693.
18. (b) Brandi, A.; Cicchi, S.; Paschetta, V.; Gomez Pardo, D.; Cossy, J. Tetrahedron Lett. 2002, 43, 9357.
19. (c) Déchamps, I.; Gomez Pardo, D.; Karoyan, P.; Cossy, J. Synlett 2005, 1170.
20. (d) Mena, M.; Bonjoch, J.; Gomez Pardo, D.; Cossy, J. J. Org. Chem. 2006, 71, 5930.
21. (e) Roudeau, R.; Gomez Pardo, D.; Cossy, J. Tetrahedron 2006, 62, 2388; and references therein.
22. (f) Déchamps, I.; Gomez Pardo, D.; Cossy, J. ARKIVOC 2007, (v), 38.
23. For comprehensive reviews, see: (g) Cossy, J.; Gomez Pardo, D. Chemtracts: Org. Chem. 2002, 15, 579.
24. (h) Cossy, J.; Gomez Pardo, D. Targets Heterocycl. Syst. 2002, 6, 1.
25. Métro, T.-X.; Gomez Pardo, D.; Cossy, J. J. Org. Chem. 2007, 72, 6556.
26. 4, filtered, and concentrated under reduced pressure. Purification of the residue by flash chromatography (silica gel, n-pentane-EtOAc) afforded the corresponding β-amino alcohol 2a-j. (14) Picq, D.; Cottin, M.; Anker, D.; Pacheco, H. Tetrahedron 1983, 39, 1797.