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. Issue 14 (30th January 2020)

• Record Type: Journal Article
• Authors: Rogier, Johann; Anani, Lilia; Coelho, Aurélien; Massicot, Fabien; Machado-Rodrigues, Carine; Behr, Jean-Bernard; Vasse, Jean-Luc
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 14(2020)
• Page Start: 2632
• Page End: 2636
• Publication Date: 2020-01-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00034e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The diastereoselective conjugate addition of chiral secondary lithium homoallylamides to α, β-unsaturated esters, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom, is reported. 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.