Carbon-Heteroatom Bond Formation by Rhi-Catalyzed Ring-Opening Reactions

Catalyzed Carbon-Heteroatom Bond Formation

Volumn , Issue , 2010, Pages 411-436

  Fleming, Matthew J ^a   Lautens, Mark ^b  

^a SOLVIAS AG   (Switzerland)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Allylic nucleophilic substitution; Carbon heteroatom bond formation; meso oxabicyclic alkenes; RhI catalysis; Ring opening; Unsymmetrical oxabicyclic alkenes; Vinyl epoxide

Indexed keywords

EID: 84884097740     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527633388.ch10     Document Type: Chapter

References (44)

1. Chen, C.-L. and Martin, S.F. (2006) J. Org. Chem., 71, 4810;
2. Arrayas, R.G., Cabrera, S., and Carretero, J.C. (2006) Synthesis, 7, 1205;
3. Rayabarapu, D.K. and Cheng, C.-H. (2007) Acc. Chem. Res., 40, 971.
4. Lautens, M., Fagnou, K., and Hiebert, S. (2003) Acc. Chem. Res., 36, 48.
5. Hogeveen, H. and Middelkoop, T.B. (1973) Tetrahedron Lett., 3671.
6. Ashworth, R.W. and Berchtold, G.A. (1977) Tetrahedron Lett., 18, 339.
7. Johnson, B.M. and Chang, P.-T.L. (1996) Analytical Profiles of Drug Substances and Excipients, Elsevier, vol. 24, 443;
8. Snyder, S.E. (1995) J.Med. Chem., 38, 2395;
9. Kamal, A. and Gayatri, L. (1996) Tetrahedron Lett., 37, 3359;
10. Kim, K., Guo, Y., and Sulikowski, G.A. (1995) J. Org. Chem., 60, 6866;
11. Perrone, R. (1995) J. Med. Chem., 38, 942.
12. Lautens, M., Fagnou, K., and Rovis, T. (2000) J. Am. Chem. Soc., 122, 5650;
13. Lautens, M., Fagnou, K., Taylor, M., and Rovis, T. (2001) J. Organomet. Chem., 624, 259.
14. Lautens, M. and Fagnou, K. (2004) Proc. Natl. Acad. Sci., 101, 5455.
15. Preetz, A., Kohrt, C., Prexter, H.-J., Torrens, A., Buschmann. H., GarciaLopez, M., Heller, D., Adv. Syn. Catal. DOI:10.1002/adsc.2000.
16. Braun,W.,Müller,W., Calmuschi, B., and Salzer, A. (2005) J. Organomet. Chem., 690, 1166.
17. Lautens, M., Fagnou, K., and Taylor, M. (2000) Org. Lett., 2, 1677.
18. Kitamura, M., Ohkuma, T., Inoue, S., Sayo, N., Kumobayashi, H., Akutagawa, S., Ohta, T., Takaya, H., and Noyori, R. (1988) J. Am. Chem. Soc., 110, 629;
19. Brenchly, G., Fedouloff, M.,Merrifield, E., and Wills, M. (1996) Tetrahedron: Asymmetry, 7, 2809.
20. Takeuchi, R. and Kitamura, N. (1998) New J. Chem., 22, 659.
21. Lautens, M. and Fagnou, K. (2001) Tetrahedron, 57, 5067.
22. Lautens, M. and Fagnou, K. (2002) Angew. Chem. Int. Ed., 41, 26.
23. Lautens, M. and Fagnou, K. (2001) J. Am. Chem. Soc., 123, 7170.
24. Lautens, M., Fagnou, K., and Yang, D. (2003) J. Am. Chem. Soc., 125, 14884.
25. Wilkinson, G. (1982) Comprehensive Organometallic Chemistry, Pergamon Press, vol. 5.
26. Lautens, M., Fagnou, K., and Zunic, V. (2002) Org. Lett., 4, 3465;
27. Cho, Y.-h., Zunic, V., Senboku, H., Olsen, M., and Lautens, M. (2006) J. Am. Chem. Soc., 128, 6837;
28. Cho, Y.-h., Fayol, A., and Lautens, M. (2006) Tetrahedron: Asymmetry, 17, 416;
29. Dockendorff, C., Jin, S., Olsen, M., Lautens, M., Coupal, M., Hodzic, L., Spear, N., Payza, K., Walpole, C., and Tomaszewski, M.J. (2009) Bioorg. Med. Chem. Lett., 19, 1228.
30. Yang, D., Long, Y.,Wang, H., andZang,Z(2008) Org. Lett., 10, 4723;
31. Yang, D., Ping, H., Long, Y., Wu, Y., Zeng, H., Wang, H., and Zuo, X. (2009) Beilstein J. Org. Chem., 5, No. 53.
32. Cho, Y.-h., Tseng, N.-W., Senboku, H., and Lautens, M. (2008) Synthesis, 15, 2467.
33. Lautens, M. and Leong, P. (2004) J. Org. Chem., 69, 2194.
34. Vallarino, L.M. and Sheargold, S.W. (1979) Inorg. Chim. Acta., 36, 243.
35. Lautens, M., Schmid, G.A., and Chau, A. (2002) J. Org. Chem., 67, 8043.
36. Fleming, M.J., Lautens, M., Thommen, M., and Spielvogel, D. (2009) PCT Int. Appl. WO 2009109648.
37. Webster, R., Böing, C., and Lautens, M. (2009) J. Am. Chem. Soc., 131, 444.
38. Wang, Q. and Padwa, A. (2004) Org. Lett., 6, 2189;
39. Wang, Q. and Padwa, A. (2006) J. Org. Chem., 71, 3210.
40. Lautens, M., Dockendorff, C., Fagnou, K., and Malicki, A. (2002) Org. Lett., 4, 1311.
41. Trost, B.M. and Crawely, M.L. (2003) Chem. Rev., 103, 2921;
42. Pfaltz, A. and Lautens, M. (1999) Chapter 24, in Comprehensive Asymmetric Catalysis, vol. 2 (eds E.N. Jacobsen, A. Pfaltz, and H. Yamamoto), Springer, Berlin.
43. Fagnou, K. and Lautens, M. (2000) Org. Lett., 2, 2319.
44. Ha, J.D., Shin, E.Y., Kang, S.K., Ahn, J.H., and Choi, J.-K. (2004) Tetrahedron. Lett., 45, 4193.