An unusual gold-catalyzed rearrangement of α-hydroxy epoxides

Catalysis Communications

Volumn 10, Issue 14, 2009, Pages 1824-1827

  Xiao, Hui Quan ^a,b   Shu, Xing Zhong ^a   Ji, Ke Gong ^a   Qi, Chen Ze ^b   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

^b SHAOXING UNIVERSITY   (China)

Author keywords

Hydroxy epoxide; Epoxide; Gold; Rearrangement

Indexed keywords

DIKETONES; EPOXIDE; HIGH YIELD; HYDROXY EPOXIDES; REARRANGEMENT; RING STRAINS; SELECTIVE FORMATION; TWO-PRODUCT; UNSYMMETRICAL;

KETONES;

GOLD;

EID: 68549128503     PISSN: 15667367     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.catcom.2009.06.008     Document Type: Article

References (28)

1. Cavda H., and Saracoglu N. Tetrahedron 65 (2009) 985
2. Asahara H., Kubo E., Togaya K., Koizumi T., Mochizuki E., and Oshima T. Org. Lett. 9 (2007) 3421
3. Snape T.J. Chem. Soc. Rev. 36 (2007) 1823
4. Jana S., Guin C., and Roy S.C. J. Org. Chem. 70 (2005) 8252
5. Henegar K.E., and Cebula M. Org. Process Res. Dev. 11 (2007) 354
6. Ahrgren L., and Sutin L. Org. Process Res. Dev. 1 (1997) 425
7. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974
8. Robinson M.W.C., Pillinger K.S., and Graham A.E. Tetrahedron Lett. 47 (2006) 5919
9. Deng X.-M., Sun X.-L., and Tang Y.-J. Org. Chem. 70 (2005) 6537
10. Hauer B., Bickley J.F., Massue J., Pena P.C., Roberts S.M.A., and Skidmore J. Can. J. Chem. 80 (2002) 546
11. So1dergren M.J., Bertilsson S.K., and Andersson P.G. J. Am. Chem. Soc. 122 (2000) 6610
12. Schurig V., and Betschinger F. Chem. Rev. 92 (1992) 873
13. Michelet V., Toullec P.Y., and Genêt J.P. Angew. Chem. Int. Ed. 47 (2008) 2
14. Muzart J. Tetrahedron 64 (2008) 5815
15. Bongers N., and Krause N. Angew. Chem. Int. Ed. 47 (2008) 2
16. Gorin D.J., and Toste F.D. Nature 446 (2007) 395
17. Hashmi A.S.K. Chem. Rev. 107 (2007) 3180
18. Zhang L.-M., Sun J.-W., and Kozmina S.A. Adv. Synth. Catal. 348 (2006) 2271
19. Yuon S.W.J. Org. Chem. 71 (2006) 2521
20. Antoniotti S., Genin E., Michelet V., and Genêt J.-P. J. Am. Chem. Soc. 127 (2005) 9976
21. Correa A., Marion N., Fensterbank L., Malacria M., Nolan S.P., and Cavallo L. Angew. Chem. Int. Ed. 46 (2007) 1
22. Yao T., Zhang X., and Larock R.C. J. Am. Chem. Soc. 126 (2004) 11164
23. Genin E., Toullec P.Y., Antoniotti S., Brancour C., Genêt J.P., and Michelet V. J. Am. Chem. Soc. 128 (2006) 3112
24. Shu X.-Z., Liu X.-Y., Xiao H.-Q., Ji K.-G., Guo L.-N., and Liang Y.-M. Chem. Eur. J. 14 (2008) 5282
25. Shu X.-Z., Liu X.-Y., Xiao H.-Q., Ji K.-G., Guo L.-N., and Liang Y.-M. Adv. Synth. Catal. 350 (2008) 243
26. Ji K.-G., Shen Y.-W., Shu X.-Z., Liu X.-Y., Xiao H.-Q., Bian Y.-J., and Liang Y.-M. Adv. Synth. Catal. 350 (2008) 1275
27. Shu X.-Z., Liu X.-Y., Xiao H.-Q., Ji K.-G., Guo L.-N., Qi C.-Z., and Liang Y.-M. Adv. Synth. Catal. 349 (2007) 2493
28. Five-membered α-hydroxy epoxides 1 m used in Scheme 1 was a mixture enantiomers. This catalytic reaction is equally effective for both trans- and cis epoxides.