Abstract
Chiral amines are formed by the highly diastereoselective intramolecular addition of alkyl and aryl radicals onto chiral mesityl sulfinimines.
Highlights
Chiral amines are formed by the highly diastereoselective intramolecular addition of alkyl and aryl radicals onto chiral mesityl sulfinimines
Chiral amines are an important class of compounds, and find uses in the fields of drug discovery, materials synthesis and natural product synthesis
Whilst there have been a large number of reports on the addition of anionic nucleophiles to both the Ellman tertbutanesulfinimines and Davis p-toluenesulfinimines,[2] relatively little work has been disclosed on the use of radical addition to these motifs
Summary
Chiral amines are formed by the highly diastereoselective intramolecular addition of alkyl and aryl radicals onto chiral mesityl sulfinimines. They showed that radical addition gave the same type of 1,2 addition products as Grignard addition, with yields in the range of 32–98% and notably high diastereoselectivity (90 - 96% de), a large excess (typically 10 eq.) of alkyl iodide radical precursor was used.
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