Chemoselective, accelerated and stereoselective aza-Michael addition of amines to N-phenylmaleimide by using TMEDA based receptors

Yuefeng Bi (1) , Laëtitia Bailly (2) , Francis Marsais (2) , Vincent Levacher (2) , Cyril Papamicaël (2) , Georges Dupas (1)

1 IRCOF - Institut de Chimie Organique Fine
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

An aza-Michael addition between a maleimide and amines is described in which the presence of simple amine receptors (TMEDA or trans-TMCDA) promote the chemoselectivity of the reaction (respectively, 1,2- and 1,4-addition). Additionally, both receptors are able to accelerate the reaction. Stoichiometries of complexes between receptors and amines were determined by 1H NMR dilution experiments while enantiomeric excesses were observed on 1,4-adducts by using (1R,2R)-TMCDA.

Domains: Chemical Sciences

Yuefeng Bi, Laëtitia Bailly, Francis Marsais, Vincent Levacher, Cyril Papamicaël, et al.. Chemoselective, accelerated and stereoselective aza-Michael addition of amines to N-phenylmaleimide by using TMEDA based receptors. Tetrahedron: Asymmetry, 2004, 15 (23), pp.3703-3706. ⟨10.1016/j.tetasy.2004.10.006⟩. ⟨hal-02378309⟩