Abstract
Several chiral amines were investigated for the stereoselective preparation of homophenylalanine derivatives using the Petasis reaction. Chiral secondary amines such as N,α-dimethylbenzylamine and N-benzylphenylglycinol gave the best results in terms of both yield and diastereoselectivity. The use of N-benzylphenylglycinol leads directly to 3-alkenyl-4-benzyl-5-phenyloxazin-2-one products. Intriguing variation was observed in the stereoselectivity of reactions employing para-substituted styrenylboronic acid substrates, where presumably only electronic factors are involved.
Conference
International Congress for Heterocyclic Chemistry (ICHC 21), International Congress on Heterocyclic Chemistry, ICHC, Heterocyclic Chemistry, 21st, Sydney, Australia, 2007-07-15–2007-07-20
References
1. doi:10.1016/S0040-4039(00)61625-8, N. A. Petasis, I. Akritopoulou. Tetrahedron Lett. 34, 583 (1993).Search in Google Scholar
2. doi:10.1039/b003067h, G. S. Currie, M. G. B. Drew, L. M. Harwood, D. J. Hughes, R. W. A. Luke, R. J. Vickers. J. Chem. Soc., Perkin Trans. 1 2982 (2000).Search in Google Scholar
3. doi:10.1039/cc9960001953, L. M. Harwood, G. S. Currie, M. G. B. Drew, R. W. A. Luke. Chem. Commun. 1953 (1996).Search in Google Scholar
4. doi:10.1016/S0040-4020(97)01028-4, N. A. Petasis, A. Goodman, I. A. Zavialov. Tetrahedron 53, 16463 (1997).Search in Google Scholar
5. doi:10.1021/ja963178n, N. A. Petasis, I. A. Zavialov. J. Am. Chem. Soc. 119, 445 (1997).Search in Google Scholar
6. doi:10.1021/ol026826i, B. Jiang, M. Xu. Org. Lett. 4, 4077 (2002).Search in Google Scholar
7. doi:10.1016/S0040-4039(01)00229-5, B. Jiang, C.-G. Yang, X.-H. Gu. Tetrahedron Lett. 42, 2545 (2001).Search in Google Scholar
8. doi:10.1016/j.tetlet.2005.01.151, K. K. Nanda, B. W. Trotter. Tetrahedron Lett. 46, 2025 (2005).Search in Google Scholar
9. doi:10.1016/S0040-4039(00)02014-1, N. A. Petasis, S. Boral. Tetrahedron Lett. 42, 539 (2001).Search in Google Scholar
10. doi:10.1016/S0040-4039(00)01717-2, N. A. Petasis, Z. D. Patel. Tetrahedron Lett. 41, 9607 (2000).Search in Google Scholar
11. doi:10.1021/ja981075u, N. A. Petasis, I. A. Zavialov. J. Am. Chem. Soc. 120, 11798 (1998).Search in Google Scholar
12. doi:10.1021/ol000195f, G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah. Org. Lett. 2, 3173 (2000).Search in Google Scholar
13. doi:10.1021/jo011116w, G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. A. Olah. J. Org. Chem. 67, 3718 (2002).Search in Google Scholar
14. doi:10.1016/j.tet.2005.09.114, T. J. Southwood, M. C. Curry, C. A. Hutton. Tetrahedron 62, 236 (2006).Search in Google Scholar
15. doi:10.1016/S0040-4039(00)00669-9, A. Golebiowski, S. R. Klopfenstein, J. J. Chen, X. Shao. Tetrahedron Lett. 41, 4841 (2000).Search in Google Scholar
16. doi:10.1016/S0040-4039(00)00668-7, S. R. Klopfenstein, J. J. Chen, A. Golebiowski, M. Li, S. X. Peng, X. Shao. Tetrahedron Lett. 41, 4835 (2000).Search in Google Scholar
17. doi:10.1002/anie.200600497, N. Kumagai, G. Muncipinto, S. L. Schreiber. Angew. Chem., Int. Ed. 45, 3635 (2006).Search in Google Scholar
18. doi:10.1016/j.tetlet.2003.11.092, N. J. McLean, H. Tye, M. Whittaker. Tetrahedron Lett. 45, 993 (2004).Search in Google Scholar
19. doi:10.1016/S0040-4039(03)01524-7, D. Naskar, A. Roy, W. L. Seibel, L. West, D. E. Portlock. Tetrahedron Lett. 44, 6297 (2003).Search in Google Scholar
20. doi:10.1016/S0040-4039(02)02619-9, D. E. Portlock, R. Ostaszewski, D. Naskar, L. West. Tetrahedron Lett. 44, 603 (2003).Search in Google Scholar
21. CCDC 675215 contains the supplementary crystallographic data for compound 5a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via <http://www.ccdc.cam.ac.uk/data_request/cif>.Search in Google Scholar
22. doi:10.1021/ma00116a020, E. Yashima, S. Huang, T. Matsushima, Y. Okamoto. Macromol. 28, 4184 (1995).Search in Google Scholar
23. doi:10.1016/S0040-4039(97)01314-2, C. A. Hutton. Tetrahedron Lett. 38, 5899 (1997).Search in Google Scholar
24. doi:10.1021/ol9906054, C. A. Hutton. Org. Lett. 1, 295 (1999).Search in Google Scholar
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