934016-33-8

Upstream product

• 132599-87-2 (6S)-2,3-didehydro-6-n-propylpiperidin-4-one 
• 501-53-1 benzyl chloroformate 
• 3238-60-6 rac-coniine 
• 1346681-71-7 (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one 
• 132599-74-7 (S)-3-Methyl-2-((S)-4-oxo-2-propyl-3,4-dihydro-2H-pyridin-1-yl)-pentanoic acid methyl ester 
• 132599-85-0 [(S)-2-Methyl-1-((S)-4-oxo-2-propyl-3,4-dihydro-2H-pyridin-1-yl)-butyl]-carbamic acid benzyl ester 
• 142764-70-3 N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one 
• 142764-69-0 N-(benzyloxycarbonyl)-(6S)-2,3-didehydro-6-n-propylpiperidin-4-one 
• 142780-95-8 N-(benzyloxycarbonyl)-(6S)-4-(1,3-dithiolan-4-yl)-6-n-propylpiperidine 

Downstream Products

• 555-92-0 (S)-coniine hydrochloride 

Relevant academic research and scientific papers

KINETIC RESOLUTION OF CHIRAL AMINES

The present invention refers to a method for the kinetic resolution of a chiral primary or secondary amine by treating the amine with a chiral, hydroxamic acid derived reagent of the formula (I). These chiral reagents are particularly useful for the kinetic resolution of cyclic amines and may be generated in situ in the presence of an N-heterocyclic carbene, thus allowing for a catalytic reaction.

Catalytic kinetic resolution of cyclic secondary amines

The catalytic resolution of racemic cyclic amines has been achieved by an enantioselective amidation reaction featuring an achiral N-heterocyclic carbene catalyst and a new chiral hydroxamic acid cocatalyst working in concert. The reactions proceed at room temperature, do not generate nonvolatile byproducts, and provide enantioenriched amines by aqueous extraction.

Enantioselective syntheses of ent-sedridine and (+)-coniine via proline-catalyzed mannich reaction

Proline-catalyzed three component Mannich reaction using 5-hydroxypentanal as a substrate was achieved in high enantioselectivity to construct a chiral center at C-2 position of 2-substituted piperidine alkaloids. The method was applied to the total syntheses of ent-sedridine and (+)-coniine.