Subscribe to RSS
DOI: 10.1055/s-2007-983789
Intramolecular Dimerizations of Cyclopentadienones
Publication History
Publication Date:
12 July 2007 (online)
Abstract
The generation of bis-cyclopentadienones joined by a tether results in the stereoselective, intramolecular dimerization of these reactive intermediates. This cycloaddition leads to structures of high molecular complexity from relatively simple starting materials.
Key words
cycloadditions - cyclopentadienones - intramolecular - dimerizations - antiaromaticity
-
1a
Pichlmair S.de Lera Ruiz M.Vilotijevic I.Paquette LA. Tetrahedron 2006, 62: 5791 -
1b
Pichlmair S.de Lera Ruiz M.Basu KI.Paquette LA. Tetrahedron 2006, 62: 5178 -
1c
Araki K.Saito K.Arimoto H.Uemura D. Angew. Chem. Int. Ed. 2004, 43: 81 -
1d
Renner MK.Jensen PR.Fenical W. J. Org. Chem. 2000, 65: 4843 -
2a
Sato S.Isobe H.Tanaka T.Ushijima T.Nakamura E. Tetrahedron 2005, 61: 11449 -
2b
Isobe H.Sato S.Tanaka T.Tokuyama H.Nakamura E. Org. Lett. 2004, 6: 3569 -
2c
Pearson AJ.Kim JB. Tetrahedron Lett. 2003, 44: 8525 -
2d
Imbriglio JE.Rainier JD. Tetrahedron Lett. 2001, 42: 6987 -
2e
Rainier JD.Imbriglio JE. Org. Lett. 1999, 1: 2037 -
2f
Jikyo T.Eto M.Harano K. J. Chem. Soc., Perkin Trans. 1 1998, 3463 - 3
Eaton PE. Angew. Chem., Int. Ed. Engl. 1992, 31: 1421 - 4
Harmata M.Barnes CL.Brackley JA.Bohnert G.Kirchhoefer P.Kürti L.Rashatasakhon P. J. Org. Chem. 2001, 66: 5232 - 5
Harmata M.Zheng P.Schreiner PR.Navarro-Vazquez A. Angew. Chem. Int. Ed. 2006, 45: 1966 - 6
Harmata M.Gomes MG. Eur. J. Org. Chem. 2006, 2273 - 7
Krafft ME.Romero RH.Scott IL. J. Org. Chem. 1992, 57: 5277 - 8
Lee BY.Kim YH.Won YC.Han JW.Suh WH.Lee IS.Chung YK.Song KH. Organometallics 2002, 21: 1500 - 9
Iqbal M.Evans P. Tetrahedron Lett. 2003, 44: 5741 - 11
Quadrelli P.Romano S.Toma L.Caramella P. J. Org. Chem. 2003, 68: 6035 - 12
Kerr WJ.McLaughlin M.Pauson PL.Robertson PSM. Chem. Commun. 1999, 2171
References
A rigorous temperature study will be performed when we have a clean cyclopentadienone precursor in hand.
13Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication number CCDC 638954(30). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road Cambridge CB2 1EZ, UK, fax: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk.