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Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines

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Abstract

The diastereoselective conjugate addition of secondary homoallylamines, obtained in the enantioenriched form via allylmetallation of imines, to α,β-unsaturated esters is reported. This method allows access to valuable building blocks as well as heterocyclic skeletons, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom.

Graphical abstract: Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines

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Article information


Submitted
07 Jan 2020
Accepted
23 Jan 2020
First published
23 Jan 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines

J. Rogier, L. Anani, A. Coelho, F. Massicot, C. Machado-Rodrigues, J. Behr and J. Vasse, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00034E

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