Primary amine catalyzed electrophilic amination of α,α-disubstituted aldehydes

Organocatalytic Enantioselective α-Nitrogenation of α,α-Disubstituted Aldehydes in the Absence of a Solvent

“…In addition, the use of 20 mol% of chiral naphthylethanamine 6 gave 12aa in 63% ee and quinine-derived amine 8 afforded 71% ee . These enantioselections are noticeably higher than those reported for similar adducts from 10q or other dialkylated aldehydes when using these catalysts under conventional solvent-including reaction conditions. ,, …”

Chiral α‐Arylethanamines: An Organocatalyst for the Enantioselective α‐Amination of Branched Aldehydes

“…We have recently successfully applied chiral proline‐derived amide thiourea bifunctional catalysts and L ‐3‐(1‐naphthyl)alanine to promote transformations of this kind, with excellent results 5f,5g. At almost the same time, Lu's5h and Greck's groups5k disclosed similar results based on 9‐amino‐9‐deoxy‐epiquinine. Up to now, all of the reported organocatalysts developed for this kind of amination, as well as other similar catalysts, have been based on a bifunctional (or multiple functional) catalytic model involving double activations, predominantly enamine/imine activations and other intra/intermolecular interactions such as hydrogen bonding and acid/base interactions, as represented by thioureas, chiral squaramides, amino acids, and their analogues 6.…”

Enantioselective Organocatalytic One‐Pot Amination/aza‐Michael/Aldol Condensation Reaction Sequence: Synthesis of 3‐Pyrrolines with a Quaternary Stereocenter

“…We have recently reported an enantioselective α‐amination of α,α‐disubstituted aldehydes 8c. In connection with this work, we became interested in the implementation of this transformation into an organocatalytic sequence to synthesize nitrogen heterocycles.…”