Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles
Cédric Spitz,
Alain G. Giuglio-Tonolo,
Thierry Terme,
Patrice Vanelle
Affiliations
Cédric Spitz
Aix-Marseille University, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, 13385 Marseille CEDEX 05, France
Alain G. Giuglio-Tonolo
Aix-Marseille University, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, 13385 Marseille CEDEX 05, France
Thierry Terme
Aix-Marseille University, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, 13385 Marseille CEDEX 05, France
Patrice Vanelle
Aix-Marseille University, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, 13385 Marseille CEDEX 05, France
A mild and metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to α,β-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-nitrobenzyl chloride 1a and α,β-unsaturated iminium salts 4 led to the formation of the 1,4-adduct with total regioselectivity.
