Pentaenolate Activation in the Organocatalytic Allylic Alkylation of Indene-2-carbaldehydes

In the manuscript, the application of pentaenolate chemistry for the allylic alkylation of indene-2-carbaldehydes with Morita-Baylis-Hillman (MBH) carbonates is described. The reaction has been realized in a highly enantio- and diastereoselective manner owing to the use of chiral tertiary amine acting as nucleophilic catalyst. Developed reactivity constitutes the first application of organocatalytic pentaenolate activation in asymmetric synthesis expanding the arsenal of catalytic methods. It leads to the formation of synthetically useful building blocks for target oriented synthesis as confirmed in selected transformations of the products.