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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Enamides and dienamides in phosphoric acid-catalysed enantioselective cycloadditions for the synthesis of chiral
Thomas Varlet1, Géraldine Masson1
1Université 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.
Abstract:
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.
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