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. 2019 Aug 21;55(65):9669-9672.
doi: 10.1039/c9cc04302k. Epub 2019 Jul 25.

Scandium catalysed stereoselective thio-allylation of allenyl-imidates

Adriano Parodi  1 , Simone Battaglioli  1 , Yang Liu  1 , Magda Monari  1 , Marta Marín-Luna  2 , Carlos Silva-López  2 , Marco Bandini  1
Affiliations

Scandium catalysed stereoselective thio-allylation of allenyl-imidates

Adriano Parodi et al. Chem Commun (Camb). .

Abstract

The site-selective thio-allylation of electron-deficient 1,2-dienes is documented under scandium catalysis. The methodology enables the realization of α-β unsaturated, β-thio, γ-allyl carboxylic acid derivatives via a one-pot Lewis acid promoted Michael addition/[3,3]-sigmatropic rearrangement sequence (20 examples) in high yields (up to 95%). Full rationalization of the reaction mechanism and stereochemical outcome is provided via DFT simulations.

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