Enantioselective Addition of Et2Zn to Benzaldehyde Activated by Benzamides Containing the (S)-a-Phenylethyl Group
DOI:
https://doi.org/10.29356/jmcs.v51i4.1291Keywords:
Atropisomers, benzamides, chiral ligands, diethylzinc, enantioselective additionAbstract
Abstract. Application of atropisomeric ligands, i.e. 2-aminobenzamides 1a–e and 2-sulfonamidobenzamides 2a–e, in the addition of
Et2Zn to benzaldehyde afforded low to moderate enantioselectivities (up to 63% ee).
Resumen. La aplicación de los ligantes atropoisoméricos, 2-aminoobenzamidas 1a–e y 2-sulfonamidobenzamidas 2a–e, en la adición
de Et2Zn a benzaldehído condujo a enantioselectividades de bajas a moderadas (hasta 63% ee).
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References
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2. Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823-2824.
3. Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. 1991, 30, 49-69.
4. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
5. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994, 255-297.
6. Soai, K.; Shibata, T. Comprehensive Asymmetric Catalysis; Jacobsen E. N., Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin,1999, 911-922.
7. Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757-824.
8. Sosa-Rivadeneyra, M.; Muñoz-Muñiz, O.; de Parrodi, C. A.; Quintero, L.; Juaristi, E. J. Org. Chem. 2003, 68, 2369-2375.
9. For recent reviews, see: (a) Brunel, J. M. Chem. Rev. 2005, 105, 857-898. (b) Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801-1836. (c) Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691-1693.
10. Eliel, E.; Wilen, S. H. Stereochemistry of Organic Compounds, John Wiley and Sons: New York, 1994, 1142-1153.
11. Bolm, C.; Hildebrand, J. P.; Muñiz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3285-3308.
12. Li, X. L.; Hewley, J. B.; Mulrooney, C. A.; Yang, J. M.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500-5511.
13. Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297-3344.
14. Curran. D. P.; Geib, S.; DeMello, N. Tetrahedron 1999, 55, 5681-5704.
15. Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295-1304.
16. Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634-2640.
17. (a) Bragg, R. A.; Clayden, J.; Morris, G. A.; Pink, J. H. Chem. Eur. J. 2002, 8, 1279-1289. (b) Clayden, J. Tetrahedron Symposiain-Print 2004, 60, 4335-4558. (c) Betson, M. S.; Clayden, J.; Helliwell, M.; Johnson, P.; Lai, L. W.; Pink, J. H.; Stimson, C. C.; Vassilion, N.; Westlund, N.; Yasin, S. A.; Youssef, L. H. Org. Biomol. Chem. 2006, 4, 424-443. (d) Marelli, C.; Monti, C.; Galli, S.; Masciocchi, N.; Piarulli, U. Tetrahedron 2006, 62, 8943-8951.
18. Rios, R.; Jimeno, C.; Carrol, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10272-10273.
19. Chan, V.; Kim, J. G.; Jimeno, C.; Carrol, P. J.; Walsh, P. J. Org. Lett. 2004, 6, 2051-2053.
20. Juaristi, E.; Escalante, J.; León-Romo, J. L.; Reyes, A. Tetrahedron: Asymmetry 1998, 9, 715-740.
21. Juaristi, E.; León-Romo, J. L.; Reyes, A. Tetrahedron: Asymmetry 1999, 10, 2441-2495.
22. Huelgas, G.; Bernès, S.; Sánchez, M.; Quintero, L.; Juaristi, E.; de Parrodi, C. A.; Walsh, P. J. Tetrahedron, 2007, 63, 12655-12664.
23. Walsh, P. J.; Li, H. M.; de Parrodi, C. A. Chem. Rev. 2007, 107, 2503-2545.
24. de Parrodi, C. A.; Walsh, P. J. Synlett 2004, 2417-2420.
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2020-07-24
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