These authors contributed equally to this work.
Gold(I)-Catalyzed Cascade Cycloadditions between Allenamides and Carbonyl-Tethered Alkenes: An Enantioselective Approach to Oxa-Bridged Medium-Sized Carbocycles†
Article first published online: 7 MAY 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 25, pages 6526–6530, June 17, 2013
How to Cite
Faustino, H., Alonso, I., Mascareñas, J. L. and López, F. (2013), Gold(I)-Catalyzed Cascade Cycloadditions between Allenamides and Carbonyl-Tethered Alkenes: An Enantioselective Approach to Oxa-Bridged Medium-Sized Carbocycles. Angew. Chem. Int. Ed., 52: 6526–6530. doi: 10.1002/anie.201302713
This work was supported by the Spanish MINECO, (SAF2010-20822-C02-01/02, and Consolider-Ingenio 2010 CSD2007-00006), ERDF funds, and Xunta de Galicia (INCITE09209084PR, GRC2010/12). H.F. acknowledges the Fundação para a Ciência e Tecnologia (Portugal) and POPH/FSE for a PhD grant (SFRH/BD/60214/2009). Johnson-Matthey and Takasago are acknowledged for a gift of metals and segphos, respectively.
- Issue published online: 11 JUN 2013
- Article first published online: 7 MAY 2013
- Manuscript Received: 2 APR 2013
- Spanish MINECO. Grant Numbers: SAF2010-20822-C02-01/02, 2010 CSD2007-00006
- Xunta de Galicia. Grant Numbers: INCITE09209084PR, GRC2010/12
- Fundação para a Ciência e Tecnologia (Portugal)
- cascade reactions;
- homogeneous catalysis;
Gold standard: Allenamides react with aldehydes or ketones having γ, δ, or ε alkenyl groups, upon activation with suitable gold catalysts, to provide oxa-bridged systems containing seven- to nine-membered carbocycles, in a formal cascade cycloaddition. By using chiral phosphoramidite/gold or bisphosphine/gold catalysts it is possible to obtain the oxa-bridged seven- and eight-membered rings with good to high enantioselectivity.