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Issue 65, 2019
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Scandium catalysed stereoselective thio-allylation of allenyl-imidates

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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.

Graphical abstract: Scandium catalysed stereoselective thio-allylation of allenyl-imidates

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Publication details

The article was received on 04 Jun 2019, accepted on 18 Jul 2019 and first published on 25 Jul 2019


Article type: Communication
DOI: 10.1039/C9CC04302K
Chem. Commun., 2019,55, 9669-9672

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    Scandium catalysed stereoselective thio-allylation of allenyl-imidates

    A. Parodi, S. Battaglioli, Y. Liu, M. Monari, M. Marín-Luna, C. Silva-López and M. Bandini, Chem. Commun., 2019, 55, 9669
    DOI: 10.1039/C9CC04302K

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