Enantioselective halogenative semi-pinacol rearrangement: A stereodivergent reaction on a racemic mixture

Chemical Communications

Volumn 50, Issue 88, 2014, Pages 13461-13464

  Romanov Michailidis, Fedor ^a   Pupier, Marion ^a   Guénée, Laure ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANOL DERIVATIVE; KETONE DERIVATIVE; SILICA GEL;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HALOGENATION; PINACOL REARRANGEMENT; RACEMIC MIXTURE; STEREOISOMERISM; THIN LAYER CHROMATOGRAPHY;

EID: 84907967260     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc05923a     Document Type: Article

References (26)

1. J. C. Fiaud and H. B. Kagan, in Top. Stereochem., ed. E. L. Eliel and S. H. Wilen, vol. 18, John Wiley and Sons, Inc., New York, 1988, pp. 249-340
2. R. P. Wurz, E. C. Lee, J. C. Ruble, G. C. Fu, Adv. Synth. Catal., 2007, 349, 2345-2352
3. V. Martin, S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, K. B. Sharpless, J. Am. Chem. Soc., 1981, 103, 6237-6240
4. M. S. VanNieuwenhze, K. B. Sharpless, J. Am. Chem. Soc., 1993, 115, 7864-7865
5. J. F. Larrow, S. E. Schaus, E. N. Jacobsen, J. Am. Chem. Soc., 1996, 118, 7420-7421
6. S. Hashiguchi, A. Fujii, K.-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem., Int. Ed. Engl., 1997, 37, 288-290
7. M. Kitamura, I. Kasahara, K. Manabe, R. Noyori, H. Takaya, J. Org. Chem., 1988, 53, 708-710
8. A. H. Hoveyda, R. R. Schrock, Chem. - Eur. J., 2001, 7, 945-950
9. G. Bredig, K. Fajans, Ber. Dtsch. Chem. Ges., 1908, 41, 752-762
10. V. S. Martin, S. S. Woodward, T. Katsuki, Y. Yamada, M. Ikeda, K. B. Sharpless, J. Am. Chem. Soc., 1981, 103, 6237-6240
11. F. Romanov-Michailidis, L. Guénée, A. Alexakis, Angew. Chem., Int. Ed., 2013, 52, 9266-9270
12. F. Romanov-Michailidis, L. Guénée, A. Alexakis, Org. Lett., 2013, 15, 5890-5893
13. S. El Baba, J.-C. Poulin, H. B. Kagan, Tetrahedron, 1984, 40, 4275-4284
14. H. B. Kagan, Tetrahedron, 2001, 57, 2449-2468
15. M. Kurosu, Y. Kishi, J. Org. Chem., 1998, 63, 6100-6101
16. J. R. Dehil, V. Gotor, J. Org. Chem., 2002, 67, 1716-1718
17. K. Tanaka, G. C. Fu, J. Am. Chem. Soc., 2003, 125, 8078-8079
18. B. M. Wang, L. Song, C. A. Fan, Y. Q. Tu, W. M. Chen, Synlett, 2003, 1497-1499
19. Z.-M. Chen, Q.-W. Zhang, Z.-H. Chen, H. Li, Y.-Q. Tu, F.-M. Zhang, J.-M. Tian, J. Am. Chem. Soc., 2011, 133, 8818-8821
20. H. Li, F.-M. Zhang, Y.-Q. Tu, Q.-W. Zhang, Z.-M. Chen, Z.-H. Chen, J. Li, Chem. Sci., 2011, 2, 1839-1841
21. M. Wang, B. M. Wang, L. Shi, Y. Q. Tu, C.-A. Fan, S. H. Wang, X. D. Hu, S. Y. Zhang, Chem. Commun., 2005, 5580-5582
22. K. Faber, Chem. - Eur. J., 2001, 7, 5005-5010
23. J. Steinreiber, K. Faber, H. Griengl, Chem. - Eur. J., 2008, 14, 8060-8072
24. H. B. Kagan, Tetrahedron, 2001, 57, 2449-2468
25. V. Rauniyar, A. D. Lackner, G. L. Hamilton, F. D. Toste, Science, 2011, 334, 1681-1684
26. M. Klussmann, L. Ratjen, S. Hoffmann, V. Wakchaure, R. Goddard, B. List, Synlett, 2010, 2189-2192