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Asymmetric [3 + 2] Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Aldehydes by Synergistic Palladium and Organocatalysis

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journal contribution
posted on 19.04.2016, 17:24 authored by Kim Søholm Halskov, Line Næsborg, Fernando Tur, Karl Anker Jørgensen
The stereoselective [3 + 2] cycloaddition between vinylcyclopropanes and α,β-unsaturated aldehydes promoted by combined palladium and organocatalysis is disclosed. The unique synergistic catalytic system allows for the stereoselective formation of highly substituted cyclopentanes with up to four stereocenters in high yields and selectivities. Vinylcyclopropanes with two different geminal substituents facilitate the formation of cyclopentanes containing a quaternary stereocenter. Furthermore, the developed reaction performs well on gram scale, and a number of transformations are demonstrated.