Preparation and supporting on solid phase of chiral auxiliary (S)-4-(4hydroxybenzyl)oxazolidin-2-one from L-tyrosinol assisted by Microwaves
DOI:
https://doi.org/10.29356/jmcs.v53i3.992Keywords:
Oxazolidinones, chiral auxiliaries, solid phase synthesis, }Abstract
An oxazolidinone chiral auxiliary, (S)-(4-Hydroxybenzyl)1,3-oxazolidin-2-one 4 was prepared in 23-80 % yield from L-tyrosinol using different methodologies. In solution, compound 4 was protected with a benzyl group on the phenolic hydroxyl 5a, which allowed the optimization of the solid phase synthesis of 5b-5d. Chiral auxiliaries 5a and 5b reacted in solution with an α,β-unsaturated system to give (S)-4-(4-(benzyloxy)benzyl)-1,3-oxazolidin-2-one 6a. By contrast, in solid phase the same reaction afforded 6b. Both reactions were carried out under microwave activation. New compounds were characterized by 1H and 13C NMR, infrared spectroscopy and mass spectrometry.
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References
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4. (a) Zhang, J.; Chen, H. N.; Chiang, F. I.; Takemoto, J. Y.; Bensaci, M.; Chang, C. W. J. Comb. Chem. 2007, 9, 17-19. (b) Barbachyn, M. R.; Ford, C. W. Angew. Chem. Int. Ed. 2003, 42, 2010-2023.
5. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835875.
6. a) Evans, D. A. Aldrichimica Acta 1982, 15, 23-32. b) Rivero, I.A.; Aceves, R. Rev. Soc. Quim. Méx. 2000, 44(2), 97-100. c) Madrigal, D.; Pina-Luis, G.; Rivero, I.A. J. Mex. Chem. Soc. 2006, 50(4) 175-179. d) Valdes, A.C.; Pina-Luis, G.; Rivero, I. A. J. Mex. Chem. Soc. 2007, 51(2), 80-88.
7. Mukhtar, T. A.; Wright, G. D. Chem. Rev. 2005, 105, 529-542.
8. Aurelio, L.; Brownlee, R. T. C.; Hughes, A. B. Chem. Rev. 2004, 104, 5823-5846.
9. (a) Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem. Int. Engl. 1997, 36, 2119–2121. (b) Waizumi, N.; Fukuyama, T. I. T. J. Am. Chem. Soc. 2000, 122, 7825–7826.
10. Renslo, A. R.; Jaishankar, P.; Venkatachalam, R.; Hackbarth, C.; López, S.; Patel, D. V.; Gordeev, M. F. J. Med. Chem. 2005, 48, 5009-5024.
11. Barbachyn, M. R.; Hutchinson, D. K.; Brickner, S. J.; Zurenko, G. E. J. Med. Chem. 1996, 39, 680-685.
12. Evans, D. A.; Gage, J. R. Organic Syntheses 1993, 8, 528-531. Wu, Y.; Shen, X. Tetrahedron: Asymmetry 2000, 11, 4359–4363.
13. Osa, Y.; Hikima, Y., Sato, Y.; Takino, K.; Ida, Y.; Hirono, S.; Nagase, H. J. Org. Chem. 2005, 70, 5737-5740.
14. Fernández, I.; Muñoz, L. Tetrahedron: Asymmetry 2006, 17, 2548–2557.
15. Mishra, R. K.; Coates, C. M; Revell, K. D.; Turos, E. Org. Lett. 2007, 9, 575-578.
16. Sun, P. C.; Sung, K. M.; Bo, S. T.; Kyu, P. D.; Hae, L. C.; Choi, D.; Koo, L. W. J. Org. Chem. 2003, 68, 43-49.
17. Faita, G.; Paio, A.; Quadrelli, P.; Rancati, F.; Senecci, P. Tetrahedron 2001, 57, 8313-8322.
18. Rivero, I. A.; Somanathan, R.; Hellberg, L. H. Synth. Commun. 1993, 23, 711-714.
19. Mitsunobu, O. Synthesis 1981, 1-28.
20. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Voguel’s, Textbook of Practical Organic Chemistry, 1989; pp. 399-410.
21. Gourlay, M. D.; Kendrick, J.; Leusen, F. J. J. Cryst. Growth Des. 2007, 7, 56-63.
22. Crystallographic Data for the structure in this paper has been deposited with the Cambridge Data Center for 4: CCDC 693196.
23. Sudharshan, M.; Hultin, P.G. Synlett 1997, 171.
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2019-06-24
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