Gohari, Seyed Jamaladdin published the artcileNovel enantioselective synthesis of (S)-ketamine using chiral auxiliary and precursor Mannich base, Synthetic Route of 343338-28-3, the main research area is chlorophenyl methylamino cyclohexanone enantioselective preparation.
Chiral auxiliaries such as tert-butanesulfinamide (TBSA) was used for the asym. synthesis of (S)-ketamine. Condensation of TBSA with ketones provides corresponding tert-butanesulfinylimine in consistently high yields. The tert-butanesulfinyl group actuates the imine for nucleophilic addition, is a potent chiral directing group, and after nucleophilic addition is easily dissociated by intervention with acid solution A Mannich base, 2-(N-piperidinomethyl)-1-phenylcyclohexylamine was synthesized via Mannich reaction starting from cyclohexanone. Then, corresponding sulfiniylimine was obtained by the condensation of TBSA with formed aminoketone. By using salts such as Ti(OEt)4, N-tert-butanesulfinylketimine was obtained in 85% yield. Next, a new chiral center was generated using Grignard reagent as nucleophile at -78° (80% yield). Finally, after many steps, the (S)-ketamine was synthesized under ozonolysis conditions with good yield and enantioselectivity (75% yield and 75% ee).
Canadian Journal of Chemistry published new progress about Amines, keto Role: SPN (Synthetic Preparation), PREP (Preparation). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Synthetic Route of 343338-28-3.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics