Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed Asymmetric Intermolecular (4 + 2) Cycloadditions of Allenamides and Dienes

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URI: http://hdl.handle.net/10347/18480
ISSN: 0002-7863
E-ISSN: 1520-5126
DOI: 10.1021/ja3065446

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2012

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American Chemical Society
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The first highly enantioselective intermolecular (4 + 2) cycloaddition between allenes and dienes is reported. The reaction provides good yields of optically active cyclohexenes featuring diverse substitution patterns and up to three stereocenters. Key to the success of the process is the use of newly designed axially chiral N-heterocyclic carbene–gold catalysts

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Francos, J., Grande-Carmona, F., Faustino, H., Iglesias-Sigüenza, J., Díez, E., Alonso, I., Fernández, R., Lassaletta, J.M., López, F. and Mascareñas, J.L. (2012). Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed Asymmetric Intermolecular (4 + 2) Cycloadditions of Allenamides and Dienes. J. Am. Chem. Soc., 134, 35, 14322-14325. doi: 10.1021/ja3065446

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This work was supported by the Spanish MINECO (SAF2010-20822-C02, CTQ2010-15297, CTQ2010-14974, and Consolider Ingenio 2010 CSD2007-00006), the ERDF funds, the Xunta de Galicia (INCITE09209084PR, GRC2010/12), and the Junta de Andalucía (2008/FQM-3833 and 2009/FQM-4537, predoctoral fellowship to F.G.-C). H.F. acknowledges the Fundação para a Ciência e Tecnologia (FCT, Portugal) and POPH/FSE for a Ph.D. grant (Grant SFRH/BD/60214/2009)

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© 2012 American Chemical Society

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Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Química Orgánica