Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2020

Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade

Résumé

A highly enantioselective synthesis of α-branched acrylonitriles is reported featuring a one-pot sequential asymmetric Michael addition/retro-Dieckmann/retro-Michael fragmentation cascade. The method, which relies on a solid, bench-stable, and commercially available acrylonitrile surrogate, is practical, scalable, and highly versatile and provides a direct access to a wide range of enantioenriched nitrile-containing building blocks. Most importantly, the method offers a new tool to incorporate an acrylonitrile moiety in an asymmetric fashion.
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Dates et versions

hal-04554473 , version 1 (22-04-2024)

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Nicolas Duchemin, Martin Cattoen, Oscar Gayraud, Silvia Anselmi, Bilal Siddiq, et al.. Direct Access to Highly Enantioenriched α-Branched Acrylonitriles through a One-Pot Sequential Asymmetric Michael Addition/Retro-Dieckmann/Retro-Michael Fragmentation Cascade. Organic Letters, 2020, 22 (15), pp.5995-6000. ⟨10.1021/acs.orglett.0c02079⟩. ⟨hal-04554473⟩
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