TBADT-Mediated Photocatalytic Stereoselective Radical Alkylation of Chiral N-Sulfinyl Imines: Towards Efficient Synthesis of Diverse Chiral Amines.

Autor: Leone M; Institut de Chimie des Substances Naturelles (ICSN) CNRS, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France., Milton JP; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland., Gryko D; Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland., Neuville L; Institut de Chimie des Substances Naturelles (ICSN) CNRS, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France.; HitCat, Seqens-CNRS joint laboratory, Seqens'Lab, 8 Rue de Rouen, 78440, Porcheville, France., Masson G; Institut de Chimie des Substances Naturelles (ICSN) CNRS, Université Paris-Saclay, 1 Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France.; HitCat, Seqens-CNRS joint laboratory, Seqens'Lab, 8 Rue de Rouen, 78440, Porcheville, France.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Apr 25; Vol. 30 (24), pp. e202400363. Date of Electronic Publication: 2024 Mar 21.
DOI: 10.1002/chem.202400363
Abstrakt: Herein we describe a sustainable and efficient photocatalytic method for the stereoselective radical alkylation of chiral sulfinyl imines. By employing readily available non-prefunctionalized radical precursors and the cost-effective TBADT as a direct HAT photocatalyst, we successfully obtain diverse chiral amines with high yields and excellent diastereoselectivity under mild conditions. This method provides an efficient approach for accessing a diverse array of medicinally relevant compounds, including both natural and synthetic α-amino acids, aryl ethyl amines, and other structural motifs commonly found in approved pharmaceuticals and natural product.
(© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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