Organic Letters

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 S_EAr: 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).