Mild and Metal-Free Diastereoselective Synthesis of N-tert-Butanesulfinylamines by Using Tetrakis(dimethylamino)ethylene

Cédric Spitz (1) , Anna Lin (1) , Thierry Terme (1) , Patrice Vanelle (1)

1 ICR - Institut de Chimie Radicalaire

A mild and metal-free diastereoselective synthesis of N-tert-butanesulfinylamines was developed by using a strategy based on tetrakis(dimethylamino)ethylene. Good yields and diastereoselectivities were achieved by addition of o-nitrobenzyl chloride or 4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitro-1H-imidazole to readily available N-tert-butanesulfinimines.

Keywords: sulfinimines; diastereoselectivity; amines; metal-free; chiral auxiliary

Domains: Chemical Sciences

Cédric Spitz, Anna Lin, Thierry Terme, Patrice Vanelle. Mild and Metal-Free Diastereoselective Synthesis of N-tert-Butanesulfinylamines by Using Tetrakis(dimethylamino)ethylene. Synthesis: Journal of Synthetic Organic Chemistry, 2014, ⟨10.1055/s-0034-1378636⟩. ⟨hal-01425582⟩