Mannich Reaction Of Imines Research Articles

ChemInform Abstract: Mannich Reaction of Imines and Silyl Enol Ethers Induced by Radical Cation Salts: Synthesis of β‐Amino Ketones.

AbstractThe Mannich reaction of imines (I) and silyl enol ether (II) and (V) induced by radical cation salt is investigated and a series of β‐amino ketones (III)/(IV) and (VI) are synthesized.

Mannich Reaction of Imines and Silyl Enol Ethers Induced by Radical Cation Salts: Synthesis of β-Amino Ketones

Mannich reaction of imines and sily enol ethers induced by radical cation salts was investigated and a series of β-amino ketones were synthesized. Reverse diastereoselectivity was obtained in the reactions of imines and silyl enol ethers of pentan-2-one and pentan-3-one, respectively, which was rationalized by quantum mechanical calculations. A single electron-transfer mechanism was proposed in which the imine radical cation acts as an electrophilic species in this transformation.

Synthesis of β-Aminoketones and Construction of Highly Substituted 4-Piperidones by Mannich Reaction Induced by Persistent Radical Cation Salts

A Mannich reaction of imines and ketones induced by persistent radical cation salts was investigated, and a series of Mannich bases, beta-aminoketones, were synthesized. A novel cyclization to form the 4-piperidone skeleton was achieved in a tandem process. The reaction can be rationalized as a radical cation process supported by various evidence.