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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Regiocontrolled Oxidative C-C Coupling of Dienol Ethers and 1,3-Dicarbonyl Compounds
Xiaoguang Liu1, Xiaohong Chen1, Justin T Mohr1
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607, United States.
Abstract:
A strategy for synthesis of γ-alkylated enones through oxidative coupling of siloxydienes and 1,3-dicarbonyl compounds is reported. This method is an interrupted form of our formal [3 + 2] cycloaddition method reported previously. The present work excels in generating all-carbon quaternary centers via C-C bond formation at the remote γ-site which is traditionally challenging to functionalize. Stereoselectivity and functional group tolerance are examined in complex systems. Double alkylation reactions are also described.
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