Expedient synthesis of chiral oxazolidinone scaffolds via rhodium-catalyzed asymmetric ring-opening with sodium cyanate

Organic Letters

Volumn 15, Issue 5, 2013, Pages 1064-1067

  Tsui, Gavin Chit ^a   Ninnemann, Nina M ^a   Hosotani, Akihito ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84874584465     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4000668     Document Type: Article

References (33)

1. Tkatchenko, I.; Jaouhari, R.; Bonnet, M.; Dawkins, G.; Lecolier, S. France Patent FR2575467, 1986; U.S. Patent 4,749,806, 1988.
2. Kianmehr, E.; Baghersad, M. H. Adv. Synth. Catal. 2011, 353, 2599
3. Vinogradova, E. V.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 11132
4. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 11430
5. Oberg, K. M.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 4785
6. Komine, Y.; Tanaka, K. Org. Lett. 2010, 12, 1312
7. Ozaki, S. Chem. Rev. 1972, 72, 457
8. Pal, P. Synlett 2012, 23, 2291
9. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
10. Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48
11. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
12. Rayabarapu, D. K.; Cheng, C.-H. Acc. Chem. Res. 2007, 40, 971
13. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
14. Lautens, M.; Fagnou, K.; Rovis, T. J. Am. Chem. Soc. 2000, 122, 5650
15. Lautens, M.; Fagnou, K.; Taylor, M.; Rovis, T. J. Organomet. Chem. 2001, 624, 259
16. Lautens, M.; Fagnou, K. J. Am. Chem. Soc. 2001, 123, 7170
17. Lautens, M.; Fagnou, K.; Yang, D. J. Am. Chem. Soc. 2003, 125, 14884
18. Lautens, M.; Fagnou, K.; Taylor, M. Org. Lett. 2000, 2, 1677
19. Lautens, M.; Fagnou, K. Tetrahedron 2001, 57, 5067
20. Leong, P.; Lautens, M. J. Org. Chem. 2004, 69, 2194
21. Tsui, G. C.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 5400
22. Zhu, J.; Tsui, G. C.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 12353
23. Lautens, M.; Fagnou, K.; Zunic, V. Org. Lett. 2002, 4, 3465
24. Webster, R.; Boyer, A.; Fleming, M. J.; Lautens, M. Org. Lett. 2010, 12, 5418
25. Lautens, M.; Fagnou, K. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5455
26. Ager, D. J.; Prakash, J.; Schaad, D. R. Chem. Rev. 1996, 96, 835
27. Ager, D. J.; Prakash, J.; Schaad, D. R. Aldrichimica Acta 1997, 30, 3
28. We have previously demonstrated strong halide effects in Rh(I)-catalyzed ARO reactions, see refs 5c, 5d, 5f, and a review: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26. The use of a Rh iodide catalyst (generated in situ using tetrabutylammonium iodide) often gave drastically improved yields and enantioselectivites. In this case, the effects were moderate (cf. Table 1, entries 6 and 7)
29. Webster, R.; Böing, C.; Lautens, M. J. Am. Chem. Soc. 2009, 131, 444
30. Preetz, A.; Kohrt, C.; Drexler, H. -J.; Torrens, A.; Buschmann, H.; Lopez, M. G.; Heller, D. Adv. Synth. Catal. 2010, 352, 2073
31. For applications of regiodivergent resolution in Rh(I)-catalyzed ARO reactions, see refs 6b, 13 and Nguyen, T. D.; Webster, R.; Lautens, M. Org. Lett. 2011, 13, 1370
32. Miura, T.; Takahashi, Y.; Murakami, M. Chem. Commun. 2007, 3577
33. Hoshino, Y.; Shibata, Y.; Tanaka, K. Angew. Chem., Int. Ed. 2012, 51, 9407