Enantioselective synthesis of oxazolidinones from N,N-dibenzylamino epoxides

Synlett

Volumn , Issue 9, 2009, Pages 1471-1473

  Vargas, Gabriel E ^a   Afonso, María M ^a   Palenzuela, J Antonio ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Amino epoxides; Cyclization; Heterocycles; Oxazolidinones

Indexed keywords

EPOXIDE; N,N DIBENZYLAMINO EPOXIDE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 67649394243     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217161     Document Type: Article

References (18)

1. Zappia, G.; Menendez, P.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Mini Rev. Med. Chem. 2007, 7, 389.
2. (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
3. (b) Evans, D. A. Aldrichimica Acta 1982, 2, 23.
4. Bergmeier, S. C. Tetrahedron 2000, 56, 2561; and references therein.
5. Zappia, G.; Gacs-Baitz, E.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Curr. Org. Synth. 2007, 4, 81.
6. Ayad, T.; Faugeroux, V.; Génisson, Y.; André, C.; Baltas, M.; Gorrichon, L. J. Org. Chem. 2004, 69, 8775.
7. Yoshida, M.; Ohshima, M.; Toda, T. Heterocycles 1993, 35, 623.
8. Osa, Y.; Hikima, Y.; Sato, Y.; Takino, K.; Ida, Y.; Hirono, S.; Nagase, H. J. Org. Chem. 2005, 70, 5737.
9. Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1995, 60, 6696.
10. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999.
11. (a) Grayson, E. J.; Davis, B. G. Org. Lett. 2005, 7, 2361.
12. (b) Bull, S. D.; Davies, S. G.; Fenton, G.; Mulvaney, A. W.; Prasad, R. S.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2000, 3765.
13. 4 and concentration, the crude reaction mixture was purified by chromatography to give the pure oxazolidinone.
14. 3: 221.1052; found: 221.1043.
15. Zappia, G.; Cancelliere, G.; Gacs-Baitz, E.; Delle Monache, G.; Misiti, D.; Nevola, L.; Botta, B. Curr. Org. Synth. 2007, 4, 238.
16. Concellón, J. M.; Suárez, J. R.; Del Solar, V. Org. Lett. 2006, 8, 349.
17. Davies, S. G.; Long, M. J. C.; Smith, A. D. Chem. Commun. 2005, 4536.
18. Each possible isomer was subjected to a conformational search using Molecular Mechanics (PCMODEL v7, Serena Software, Bloomington, IN). The coupling constants in each conformer were calculated and the Boltzmann weighted average was used for the comparison with the experimental values.