Chiral imines on the wave: reactivity of <em>tert</em>-butyl acrylate and stereoselectivity determination using NMR in liquid crystals - Archive ouverte HAL Accéder directement au contenu
Communication Dans Un Congrès Année : 2015

Chiral imines on the wave: reactivity of tert-butyl acrylate and stereoselectivity determination using NMR in liquid crystals

Résumé

In connection with synthetic applications, we have foreseen to study the reactivity of the poorly reactive $tert$-butyl acrylate electrophile with chiral imines of unsymmetrical ketones, using conventional or microwave flash heating under carefully controlled reaction conditions in order to develop a selective and efficient access to the corresponding Michael adducts in which a created stereogenic quaternary carbon center was fully stereocontrolled. Depending on the conditions, either a keto ester or a lactam were obtained. A good correlation was obtained between experiment and theoretical calculations. The stereoselectivity of the process (e>95%) was determined using natural abundance $^{13}$C-{$^1$H} NMR in a chiral polypeptide liquid crystal. The scope of the reaction was screened using a set of electrophilic alkenes giving Michael adducts in good yield and similar high enantiocontrol.
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Dates et versions

hal-02314359 , version 1 (14-10-2019)

Identifiants

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Lucie Vandromme, Li Chen, Lai Wei, Franck Le Bideau, André Loupy, et al.. Chiral imines on the wave: reactivity of tert-butyl acrylate and stereoselectivity determination using NMR in liquid crystals. MOL2NET, International Conference on Multidisciplinary Sciences, 2015, SCIForum, France. pp.1-18, ⟨10.3390/MOL2NET-1-a003⟩. ⟨hal-02314359⟩
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