912358-38-4

Upstream product

• 627-31-6 1,3-Diiodopropane 
• 2386-64-3 ethylmagnesium chloride 
• 178313-97-8 (S)-N-(1-phenylethyl)-2-methylideneaziridine 
• 912358-37-3 1-[(1S)-phenylethyl]-2-propylpiperidine-2-carbonitrile 
• 107-87-9 2-Pentanone 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 7529-63-7 (1'S)-(-)-1-(1'-phenylethyl)piperidine 
• 111-24-0 1,5-dibromo-pentane 
• 912358-35-1 1-[(1S)-1-phenylethyl]piperidine-2-carbonitrile 
• 126017-67-2 (6R)-(-)-1-<(1S)-1-Phenylethyl>-5-propyl-2-piperidinone 

Relevant academic research and scientific papers

Anodic cyanation of (S)-(-)-1-1(1-phenylethyl)piperidine: An expeditious synthesis of (S)-(+)-coniine

A short and efficient asymmetric synthesis of enantiopure (S)-(+)-coniine is reported. Anodic cyanation of (-)-1-[(1S)-1-phenylethyl]piperidine, derived from [(1S)-1-phenylethyl]amine, results in regioselective formation of the corresponding α-amino-nitrile, which was alkylated with propyl iodide to give a bifunctional derivative. The latter underwent a stereoselective reductive decyanation (80% de), the product of which was hydrogenolyzed to afforded (S)-(+)-coniine (99% ee) with an overall 35% yield from (-)-1 -[(1S)-1-phenylethyl]piperidine. Georg Thieme Verlag Stuttgart.

Asymmetric synthesis of 2-substituted piperidines using a multi-component coupling reaction: Rapid assembly of (S)-coniine from (S)-1-(1-phenylethyl)-2-methyleneaziridine

(S)-Coniine is made using a reaction which assembles the piperidine ring by the sequential formation of four new chemical bonds and installs the C-2 stereogenic centre with high levels of diastereocontrol (90% de).

A new asymmetric synthesis of (S)-(+)-pipecoline and (S)-(+)- and (R)-(-)-coniine by reductive photocyclization of dienamides

(S)-(+)-Pipecoline and both enantiomers of coniine were synthesized, in good yields, by a reductive photocyclization of chiral dienamides. Enantioselectivities of up to 75% were obtained. (C) 2000 Published by Elsevier Science Ltd.