Gold-catalyzed ring expansions of 1-alkynylcyclobutanol derivatives via tandem hydration and α-ketol rearrangement

Tetrahedron

Volumn 68, Issue 26, 2012, Pages 5241-5247

  Kim, Ki Dae ^a   Yeom, Hyun Suk ^a   Shiin, Sunwoong ^a   Shin, Seunghoon ^a  

^a Hanyang University   (South Korea)

Author keywords

Hydroxycyclopentanone; Ketol rearrangement; Gold catalysis; Ring expansion; Tandem reaction

Indexed keywords

ALKYNYL GROUP; BUTANOL; CYCLOPENTANONE DERIVATIVE; GOLD; KETOL; WATER;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDRATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 84861686853     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.018     Document Type: Article

References (29)

1. T. Seiser, T. Saget, D.N. Tran, and N. Cramer Angew. Chem., Int. Ed. 50 2011 7740
2. E. Leemans, M. D'hooghe, and N. De Kimpe Chem. Rev. 111 2011 3268
3. Q.W. Zhang, C.A. Fan, H.J. Zhang, Y.Q. Tu, Y.M. Zhao, P. Gu, and Z.M. Chen Angew. Chem., Int. Ed. 48 2009 8572
4. E. Zhang, C.-A. Fan, Y.-Q. Tu, F.-M. Zhang, and Y.-L. Song J. Am. Chem. Soc. 131 2009 14626
5. B.M. Trost, J. Xie, and N. Maulide J. Am. Chem. Soc. 130 2008 17258
6. A. Chen, R. Lin, Q. Liu, and N. Jiiao Chem. Commun. 2009 6842
7. M. Yoshida, M. Sugimoto, and M. Ihara Tetrahedron Lett. 42 2011 3877
8. K. Sugimoto, M. Yoshida, and M. Ihara Synlett 2006 1923
9. N. Iwasawa, T. Matsuo, M. Iwanoto, and T. Ikeno J. Am. Chem. Soc. 120 1998 3930
10. D. Garayalde, and C. Nevado Beilstein J. Org. Chem. 7 2011 767
11. J.P. Markham, S.T. Staben, and F.D. Toste J. Am. Chem. Soc. 127 2005 9708
12. F. Kleinbeck, and F.D. Toste J. Am. Chem. Soc. 131 2009 9178
13. C.-W. Li, K. Pati, G.-Y. Lin, S.M.A. Sohel, H.-H. Hung, and R.-S. Liu Angew. Chem., Int. Ed. 49 2010 9891
14. S. Ye, and Z.-X. Yu Org. Lett. 12 2010 804
15. H.-S. Yeom, S.-J. Yoon, and S. Shin Tetrahedron Lett. 48 2007 4817
16. B. Crone, and S.F. Kirsch Chem. - Eur. J. 14 2008 3514
17. Y. Fukuda, and K. Utimoto J. Org. Chem. 56 1991 3729
18. J.H. Teles, S. Brode, and M. Chabanas Angew. Chem., Int. Ed. 37 1998 1415
19. M. Lein, M. Rudolph, and A.S.K. Hashmi Organometallics 29 2010 2206
20. C.M. Krauter, A.S.K. Hashmi, and M. Pernpointner ChemCatChem 2 2010 1226
21. A. Corma, A. Leyva-Pérez, and M.J. Sabater Chem. Rev. 111 2011 1657
22. A. Duschek, and S.F. Kirsch Angew. Chem., Int. Ed. 50 2011 1524
23. S.I. Lee, J.Y. Baek, S.H. Sim, and Y.K. Chung Synthesis 2007 2107
24. D.A. Engel, and G.B. Dudley Org. Biomol. Chem. 7 2009 4149
25. A.L. Ringer, and D.H. Magers J. Org. Chem. 72 2007 2533
26. L.A. Paquette, D.R. Owen, R.T. Bibart, C.K. Seekamp, A.L. Kahane, J.C. Lanter, and M.A. Corral J. Org. Chem. 66 2001 2828
27. L.A. Paquette, M.J. Kinney, and U. Dullweber J. Org. Chem. 62 1997 1713
28. D.D. Perrin, and W.I.F. Armarego Purification of Laboratory Chemicals 4th ed. 1996 Butterworth-Heinemann Oxford
29. B.M. Trost, J.L. Gunzner, and T. Yasukata Tetrahedron Lett. 42 2001 3775