Kadriye AYDIN, Stephen T. ASTLEY, Gamze KOZ, Leman KARADENİZ

Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: reversal of enantioselectivity and rate acceleration on addition of $AICl_3$

Using asymmetric Cobalt(III) salen catalysts, the ring-opening of epichlorohydrin by 2,3-dihydroxybenzaldehyde and 2,4- dihydroxybenzaldehyde was found to occur at the phenolic groups most distant from the aldehydic group. Switching catalysts afforded a reversal in enantioselectivity. For 2,3-dihydroxybenzaldehyde and salicylaldehyde, addition of $AICI _3$to the reaction mixture led to an increase in reaction rate without any decrease in product enantiopurity.

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1. Lukowska, E.; Plenkiewicz, J. Tetrahedron: Asymmetry 2007, 18, 1202.
2. Zhou, Z.-T.; Xie, J.H.; Zhou, Q.-L. Adv. Synth. Cat. 2009, 351, 363.
3. Liu, Y.-H.; Liu, Q.-S.; Zhang, Z.-H. J. Mol. Cat. A: Chem. 2008, 296, 42.
4. Alam, M. M.; Varala, R. Enugala, R.; Srinivas, R. A. Lett. Org. Chem. 2006, 3, 187.
5. Sun, J.; Gu, W.; Huang, Y.; Pan, X.; Zhu, C. Lett. Org. Chem. 2009, 6, 329
6. Zakavi, S.; Karimipour, G. R.; Gharab, N. G. Cat. Commun. 2009, 10, 388.
7. Das, B.; Krishnaiah, M.; Thirupathi, P. Laxminarayana, K. Tetrahedron Lett. 2007, 48, 4263.
8. Iranpoor, N.; Firouzabadi, H.; Safavi, A.; Shekarriz, M. Synth. Commun. 2002, 32, 2287.
9. Surendra, K.; Krishnaveni, N. S.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 4994.
10. Tamami, B.; Iranpoor, N.; Rezaei, R. Synth. Commun. 2004, 34, 2789.
11. Lida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H.-G. Shibasaki, M. Angew. Chem. Int. Ed. 1998, 37, 2223.
12. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086.
13. Peukert, S.; Jacobsen, E. N. Org. Lett. 1999, 1, 1245.
14. Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687.
15. Ready, J. M.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2002, 41, 1374.
16. Kawthekar, R. B.; Ahn, C.-H.; Kim, G.-J. Catal. Lett. 2007, 115, 62.
17. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307.
18. Kumar, P.; Naidu, V.; Gupta, P. Tetrahedron, 2007, 63, 2745.
19. Ley, J. P.; Bertram, H.-J. Bioorg. Med. Chem. 2001, 9, 1879.
20. Iranpoor, N.; Firouzabadi, H.; Nowrouzi, N. Tetrahedron Lett. 2006, 47, 8247.
21. Larrow, J. F.; Jacobsen, E. N. Topics Organmet. Chem. 2004, 6, 123.
22. Kim, D. H.; Shin, U. S.; Song, C. E. J. Mol. Cat. A: Chem. 2007, 271, 70.
23. Sancho, M. I.; Jubert, A. H.; Blanco, S. E.; Ferretti, F. H.; Castro, E. A. Spectrochim. Acta Part A, 2007, 68, 387.
24. Gou, S.; Zhou, X.; Wang, J.; Liu, X.; Feng, X. Tetrahedron, 2008, 64, 2864.
25. Pineschi, D. M.; Bertolini, F.; Haak, R. M.; Crotti, P.; Macchia, F. Chem. Commun. 2005, 1426.
26. Nielsen, L. P. C.; Stevenson, C. P.; Blackmond, D. G.; Jacobsen, E. N. J. Am. Chem. Soc., 2004, 126, 1360.