Synlett
DOI: 10.1055/s-0036-1590922
letter
© Georg Thieme Verlag Stuttgart · New York

Radical Allylation: E-Selective Radical Conjugate Addition–Elimination Reaction from Morita–Baylis–Hillman Adducts

Cyril Lebargy, Coralie De Schutter, Remi Legay, Emmanuel Pfund, Thierry Lequeux*
  • Normandie University, Laboratoire de Chimie Moléculaire et Thioorganique UMR 6507, ENSICAEN, UNICAEN, CNRS, 6 Bd. du Maréchal Juin, 14050 Caen, France   Email: thierry.lequeux@ensicaen.fr
This work was supported by the excellence laboratory LabEx SYNORG (ANR-11-LABX-0029), the Conseil Régional de Normandie, and the European FEDER fundings.
Further Information

Publication History

Received: 28 July 2017

Accepted after revision: 07 September 2017

Publication Date:
27 September 2017 (eFirst)

Abstract

Triethylborane-mediated radical allylation was performed from Morita–Baylis–Hillman alcohols with no need of protecting group. The radical conjugated addition–elimination reaction is highly selective, and trisubstituted E-alkenes were obtained. This reaction opened a new route for the preparation of functionalized α,β-unsaturated ketones.

Supporting Information