Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO4 and chiral cinchona ligands in the absence of co-oxidant
Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO4 and chiral cinchona ligands in the absence of co-oxidant
For the first time, removal of oxygen atoms from allylic hydroperoxide functionality and reintroduction to the double bond was achieved using catalytic OsO4 and chiral cinchona alkaloid derivatives in an acetone water mixture to give corresponding chiral 1/2,3-triol with an enantioselectivity up to 99% ee. The hydroperoxide group was used as both a co-oxidant and a source of hydroxyl groups. This protocol is thought to have potential to provide opportunities for chiral synthesis of 1/2,3-triols from corresponding allylic hydroperoxides in the absence of co-oxidant in one stage for the first time in the literature.
___
- 1. Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C-H. Chem. Rev. 1996, 96, 443474.
- 2. Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779844.
- 3. G¨ultekin, M. S.; C¸ elik, M.; Balcı, M. Current Org. Chem. 2004, 8, 1159.
- 4. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683.
- 5. Yang, C. Y.; Chen, M. C.; Peter, C. J. Am. Chem. Soc. 1984, 106, 7310.
- 6. Duchek, J.; Adams, D. R.; Hudlicky, T. Chem. Rev. 2011, 111, 42234258.
- 7. Rouf, A.; Taneja, S. C. Chirality 2014, 26, 6378.
- 8. Arjona, O.; G´omez, A. M.; Crist´obal L´opez, J.; Plumet, J. Chem. Rev. 2007, 107, 19192036.
- 9. Ikai, T.; Okamoto, Y. Chem. Rev. 2009, 109, 60776101.
- 10. Zahran, M. A. H.; Salem, T. A. R. Samaka, R. M.; Agwa, H. S.; Awad, A. R. Bioorg. Med. Chem. 2008, 16, 97089718.
- 11. Brent, R. L. J. Pediatr. 1964, 64, 762770.
- 12. Ohshima, T.; Nemoto, T.; Tosaki, S.; Kakei, H.; Gnanadesikan, V.; Shibasaki, M. Tetrahedron 2003, 59, 10485 10497.
- 13. Wang, Y.; Wu, Z.; Li, Z.; Zhou, X. Tetrahedron Lett. 2009, 50, 25092511.
- 14. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 39433946.
- 15. Burns, P. A.; Foote, C. S. J. Am. Chem. Soc. 1974, 106, 43394342.
- 16. Sharpless, K. B. Tetrahedron 1994, 50, 42354258.
- 17. Dapurkar, E. S.; Kawanami, H.; Komura, K.; Yokoyama, T.; Ikushima, Y. Appl. Catal. A: Gen. 2008, 346, 112115.
- 18. Ganem, B.; Schulte, G. R. Tetrahedron Lett. 1982, 23, 289292.
- 19. Se¸cen, H.; G¨ultekin, M. S.; S¨utbeyaz, Y.; Balcı, M. Turk J. Chem. 1993, 17, 108113.
- 20. Kolb, H. C.; Van-Nieuwenhze, M. S.; Sharpless K. B. Chem. Rev. 1994, 94, 24832547.
- 21. Barrulas, P.; Benaglia, M.; Burke, A. J. Tetrahedron: Asymmetry 2014, 25, 923935.
- 22. Alp, C.; Atmaca, U.; C¸ elik, M.; G¨ultekin, M. S. Synlett 2009, 27652768.
- 23. G¨oksu, H.; Dalmizrak, D.; Akbayrak, S.; G¨ultekin, M. S.; Ozkar, S.; Metin, ¨ O. ¨ J. Mol. Catal. A Chem. 2013, 378, 142147.
- 24. Frimer, A. A. J. Org. Chem. 1977, 42, 31943196.
- 25. Adam, W.; Epe, B.; Schiffmann, D.; Vargas, F.; Wild, D. Angew. Chem. 1988, 100, 443445.
- 26. Murty, R. S.; Bio, M.; You, Y. Tetrahedron Lett. 2009, 50, 10411044.
- 27. Chambers, R. D.; Sandford, G.; Shah, A. Synth. Commun. 1996, 26, 18611866.
- 28. Yoshihiko, D.; Shoji, H.; Tadao, H.; Yoshihisa, I.; Akira, T. J. Chem. Soc., Perkin Trans. 2 1989, 275282.
- 29. Yoshihisa, I.; Toshihiko, U.; Tadao, H. J. Chem. Soc., Perkin Trans. 2 1984, 20532056.
- 30. Lee, Y. T.; Fisher, J. F. Bioorg. Chem. 2000, 28, 163175.
- 31. Fulvia, O.; Francesca, P. Tetrahedron: Asymmetry 1996, 7, 10331040.
- 32. Mandel, M.; Hudlicky, T. Synlett 1993, 6, 418420.