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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
Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02378309
Contributor : Laetitia Bailly <>
Submitted on : Monday, November 25, 2019 - 10:17:35 AM
Last modification on : Thursday, July 2, 2020 - 3:30:09 AM

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COMUE-NORMANDIE | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | CNRS | ENSICAEN | UNILEHAVRE | UNICAEN

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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, Elsevier, 2004, 15 (23), pp.3703-3706. ⟨10.1016/j.tetasy.2004.10.006⟩. ⟨hal-02378309⟩

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