Unexpected diastereoselective one-pot assembly of hexahydroazulenones from 2-alkylcyclohexanones and arylacetylenes in KOH/DMSO suspension

Tetrahedron Letters

Volumn 52, Issue 33, 2011, Pages 4285-4287

  Trofimov, Boris A ^a   Schmidt, Elena Yu ^a   Skitaltseva, Elena V ^a   Zorina, Nadezhda V ^a   Protsuk, Nadezhda I ^a   Ushakov, Igor A ^a   Mikhaleva, Albina I ^a   Dyachenko, Oleg A ^b   Kazheva, Olga N ^b   Aleksandrov, Grigorii G ^c  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

^c KURNAKOV INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Russian Federation)

Author keywords

2 Alkylcyclohexanones; Arylacetylenes; Azulenones; Vinyl ketones

Indexed keywords

ACETYLENE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; DIMETHYL SULFOXIDE; KETONE DERIVATIVE; POTASSIUM HYDROXIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 79960213715     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.06.019     Document Type: Article

References (17)

1. D.A. Colby, R.G. Bergman, and J.A. Ellman Chem. Rev. 110 2010 624
2. B. Karimi, H. Behzadna, D. Elhamifar, P.F. Akhavan, and F.K. Esfahani Synthesis 2010 1399
3. X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem. Int. Ed. 48 2009 5094
4. C.-J. Li Acc. Chem. Res. 42 2009 335
5. D.G. Brown, T.R. Hoye, and R.G. Brisbois J. Org. Chem. 63 1998 1630
6. H. Wang, K. Michalak, M. Michalak, G. Jimenez-Oses, J. Wicha, and K.N. Houk J. Org. Chem. 75 2010 762
7. O.L. Epstein, and J.K. Cha Angew. Chem. Int. Ed. 44 2005 121
8. M. Fujiwara, K. Ijichi, K. Tokuhisa, K. Katsuura, G.-Y.-S. Wang, D. Uemura, S. Shigeta, K. Konno, T. Yokota, and M. Baba Antiviral Chem. Chemother. 7 1996 230
9. M. Fujiwara, K. Ijichi, K. Tokuhisa, K. Katsuura, S. Shigeta, K. Konno, G.Y.S. Wang, D. Uemura, T. Yokota, and M. Baba Antimicrob. Agents Chemother. 40 1996 271
10. S. O'Keeffe, F. Harrington, and A.R. Maguire Synlett 2007 2367
11. A.R. Maguire, P. O'Leary, F. Harrington, S.E. Lawrence, and A.J. Blake J. Org. Chem. 66 2001 7166
12. A.R. Maguire, N.R. Buckley, P. O'Leary, and G. Ferguson J. Chem. Soc., Perkin Trans. 1 1998 4077
13. A. Padwa, K.E. Krumpe, Y. Gareau, and U. Chiacchiot J. Org. Chem. 56 1991 2523
14. C.B. Ivchenko, P.V. Ivchenko, I.E. Nifant'ev, L.A. Kashulin, L.V. Taidakov, and L.G. Kuz'mina Russ. Chem. Bull. 49 2000 724
15. A.E. Favorsky Zh. Ross. Khim. Obshch. 37 1906 643
16. M. Smith, and J. March March's Advanced Organic Chemistry 6th ed. 2007 Wiley New York p 1360
17. Atomic coordinates, bond lengths, bond angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre (CCDC). These data can be obtained free of charge via www.ccdc.cam.uk.conts/retrieving.html or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk). Any request to the CCDC for data should quote the full literature citation and CCDC reference number CCDC 826323.