Scandium catalysed stereoselective thio-allylation of allenyl-imidates.

Author(s) Parodi, A.; Battaglioli, S.; Liu, Y.; Monari, M.; Marín-Luna, M.; Silva-López, C.; Bandini, M.
Journal Chem Commun (Camb)
Date Published 2019 Aug 21

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.

DOI 10.1039/c9cc04302k
ISSN 1364-548X
Citation Chem Commun (Camb). 2019;55(65):96699672.