Abstract
Deprotonation of terminal epoxides and aziridines with organolithium/diamine combinations or lithium amides allows the regio- and stereoselective formation of α-lithiated species. Judicious choice of reaction conditions allows these species to operate as nucleophiles, enolate equivalents, vinyl cation equivalents, or carbenes.
Conference
International Conference on Organic Synthesis (ICOS-16), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 16th, Mérida, Yucatán, México, 2006-06-11–2006-06-15
References
1. doi:10.1002/3527607862.ch5, D. M. Hodgson, C. D. Bray. In Aziridines and Epoxides in Organic Synthesis, A. K. Yudin (Ed.), pp. 145–184, Wiley-VCH, Weinheim (2006).Search in Google Scholar
2. doi:10.1021/jo00877a022, J. J. Eisch, J. E. Galle. J. Org. Chem. 41, 2615 (1976).Search in Google Scholar
3. doi:10.1016/S0040-4039(00)74841-6, P. Lohse, H. Loner, P. Acklin, F. Sternfeld, A. Pfaltz. Tetrahedron Lett. 32, 615 (1991).Search in Google Scholar
4. doi:10.1021/ol006948f, D. M. Hodgson, S. L. M. Norsikian. Org. Lett. 3, 461 (2001).Search in Google Scholar
5. doi:10.1055/s-2004-829083, D. M. Hodgson, E. H. M. Kirton. Synlett 1610 (2004).Search in Google Scholar
6. D. M. Hodgson, N. J. Reynolds, S. J. Coote. Org. Lett. 6, 4187 (2004).10.1021/ol048544jSearch in Google Scholar
7. doi:10.1039/b502888d, D. M. Hodgson, E. H. M. Kirton, S. M. Miles, S. L. M. Norsikian, N. J. Reynolds, S. J. Coote. Org. Biomol. Chem. 3, 1893 (2005).Search in Google Scholar
8. doi:10.1039/c39940002103, A. Yanagisawa, K. Yasue, H. Yamamoto. J. Chem. Soc., Chem. Commun. 2103 (1994).Search in Google Scholar
9. doi:10.1016/S0040-4039(02)01893-2, D. M. Hodgson, N. J. Reynolds, S. J. Coote. Tetrahedron Lett. 43, 7895 (2002).Search in Google Scholar
10. doi:10.1021/ol050060f, D. M. Hodgson, P. G. Humphreys, J. G. Ward. Org. Lett. 7, 1153 (2005).Search in Google Scholar
11. doi:10.1021/ja031770o, D. M. Hodgson, C. D. Bray, N. D. Kindon. J. Am. Chem. Soc. 126, 6870 (2004).Search in Google Scholar
12. doi:10.1021/ja00993a052, J. K. Crandall, L.-H. C. Lin. J. Am. Chem. Soc. 89, 4527 (1967).Search in Google Scholar
13. doi:10.1021/ja045513a, D. M. Hodgson, M. J. Fleming, S. J. Stanway. J. Am. Chem. Soc. 126, 12250 (2004).Search in Google Scholar
14. doi:10.1021/jo01293a033, K. L. Dhawan, B. D. Gowland, T. Durst. J. Org. Chem. 45, 922 (1980).Search in Google Scholar
15. doi:10.1021/ol050402h, D. M. Hodgson, C. D. Bray, N. D. Kindon. Org. Lett. 7, 2305 (2005).Search in Google Scholar
16. doi:10.1002/anie.200503303, D. M. Hodgson, S. M. Miles. Angew. Chem., Int. Ed. 45, 935 (2006).Search in Google Scholar
17. doi:10.1021/ja00993a051, J. K. Crandall, L.-H. C. Lin. J. Am. Chem. Soc. 89, 4526 (1967).Search in Google Scholar
18. doi:10.1021/ja047346k, D. M. Hodgson, Y. K. Chung, J. M. Paris. J. Am. Chem. Soc. 126, 8664 (2004).Search in Google Scholar
19. doi:10.1055/s-2005-869973, D. M. Hodgson, Y. K. Chung, J. M. Paris. Synthesis 2264 (2005).Search in Google Scholar
20. doi:10.1021/ol060101n, D. M. Hodgson, P. G. Humphreys, J. G. Ward. Org. Lett. 8, 995 (2006).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston
