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Organic Letters [SOPhy]

Mar 1 2019

Abstract :

Two unprecedented domino reactions are described, starting from ketospiro-enesulfonamides. By treatment with ZrCl4 and allylsilane, an intramolecular electrophilic aromatic substitution and subsequent allylation is observed. By treatment with TiCl4 and allylsilane, a double enamine-type reaction takes place, thus creating simultaneously four contiguous stereogenic centers diastereoselectively.



Reference :

Frédéric Beltran and Laurence Miesch

Tertiary Enamide-Triggered SEAr: Domino Allylation and Enamine-Type Addition

Organic Letters, Published 26th February, 2019 (web) - DOI: 10.1021/acs.orglett.8b03987


Contact chercheur :

Laurence Miesch, équipe SOPhy, Institut de Chimie (UMR 7177).