Issue 14, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
07 Jan 2020
Accepted
23 Jan 2020
First published
23 Jan 2020

Org. Biomol. Chem., 2020,18, 2632-2636

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, 18, 2632 DOI: 10.1039/D0OB00034E

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