Enamides and dienamides in phosphoric acid-catalysed enantioselective cycloadditions for the synthesis of chiral amines.


Journal

Chemical communications (Cambridge, England)
ISSN: 1364-548X
Titre abrégé: Chem Commun (Camb)
Pays: England
ID NLM: 9610838

Informations de publication

Date de publication:
27 Apr 2021
Historique:
entrez: 28 4 2021
pubmed: 29 4 2021
medline: 29 4 2021
Statut: ppublish

Résumé

Chiral substituted cyclic amines are ubiquitous among biologically active molecules and natural products and are valuable intermediates in organic synthesis. Stable and easy to synthesize enamides and dienamides are versatile building blocks for the preparation of chiral amines. The exceptional synergy displayed between these synthetic synthons and chiral phosphoric acid catalysts has successfully been harnessed to develop straightforward formal cycloadditions exhibiting notably high enantiocontrol. This feature article showcases the remarkable versatility of these cycloadditions to access chiral cyclic amines with different ring sizes ranging from 5- to 7-membered rings, with an emphasis on biologically active natural products.

Identifiants

pubmed: 33908458
doi: 10.1039/d1cc00590a
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

4089-4105

Auteurs

Thomas Varlet (T)

Université Paris-Saclay, Institut de Chimie des Substances Naturelles, ICSN-CNRS UPR 2301, 1 av. de la Terrasse, 91198 Gif-sur-Yvette, France. geraldine.masson@cnrs.fr geraldine.masson@universite-paris-saclay.fr.

Géraldine Masson (G)

Université Paris-Saclay, Institut de Chimie des Substances Naturelles, ICSN-CNRS UPR 2301, 1 av. de la Terrasse, 91198 Gif-sur-Yvette, France. geraldine.masson@cnrs.fr geraldine.masson@universite-paris-saclay.fr.

Classifications MeSH