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

• Published in: Tetrahedron: asymmetry Vol. 15; no. 23; pp. 3703 - 3706
• Main Authors: Bi, Yuefeng, Bailly, Laëtitia, Marsais, Francis, Levacher, Vincent, Papamicaël, Cyril, Dupas, Georges
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 29-11-2004; Elsevier
• Subjects: Chemical Sciences
• ISSN: 0957-4166; 1362-511X; 0957-4166
• DOI: 10.1016/j.tetasy.2004.10.006

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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 (1
R,2
R)-TMCDA.