Scandium catalysed stereoselective thio-allylation of allenyl-imidates. Issue 65 (25th July 2019)

• Record Type: Journal Article
• Authors: Parodi, Adriano; Battaglioli, Simone; Liu, Yang; Monari, Magda; Marín-Luna, Marta; Silva-López, Carlos; Bandini, Marco
• Is Part Of: Chemical communications. Volume 55:Issue 65(2019)
• Page Start: 9669
• Page End: 9672
• Publication Date: 2019-07-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc04302k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The site-selective thio-allylation of electron-deficient 1, 2-dienes is documented under scandium catalysis. 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.