Highly Efficient Asymmetric Aziridination of Unsaturated Aldehydes Promoted by Chiral Hetero‐organic Catalysts

Abstract

Optically pure hetero‐organic catalysts that bear a hydroxyl moiety, a stereogenic sulfinyl group, and a chiral amine moiety, are highly efficient in the asymmetric aziridination of unsaturated aldehydes and lead to the desired chiral products in high yields (up to 93 %) with enantiomeric excess values up to 92 %. The influence of the stereogenic centers at the sulfinyl sulfur atom and in the amine moiety on the stereochemical outcome of the title reaction is discussed.

Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis

“…The most efficient catalysts were sulfoxides 46c,d bearing enantiomeric ( S )- or ( R )-1-(1′-naphthyl)­ethylamine moiety, respectively. Again, the stereogenic centers located in the amino moieties exerted a decisive influence on the absolute configuration of the products …”

“…Again, the stereogenic centers located in the amino moieties exerted a decisive influence on the absolute configuration of the products. 65 2.9.5. Polydentate Sulfinyl Catalysts Bearing Prolinol Moiety.…”

Asymmetric Organocatalytic Aziridination: Recent Advances

“…In the realm of amine derivatives, Kiełbasinski et al. developed the chiral tridentate ligand 78 bearing hydroxyl, sulfinyl, and amine moieties that efficiently catalysed the asymmetric aziridination of α,β‐unsaturated aldehyde 77 (Scheme ). Specifically, the two stereogenic centres at the sulfinyl sulfor atom and at the carbon atom in the amine function decisively influenced the absolute configuration of the products 79 , which were obtained in moderate to good yields (37–93%) and remarkable stereoselectivity (up to 15 : 1 d.r., up to 92% ee ).…”