326477-54-7

Upstream product

• 326477-52-5 Methyl (R_S,S)-(-)-3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 253665-35-9 (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide 
• 130573-43-2 (2,2-dimethyl-6-methylene-6H-1,3-dioxin-4-yloxy)trimethylsilane 
• 385435-07-4 4-ethoxy-6-phenyl-5,6-dihydro-1H-pyridin-2-one 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 1357361-01-3 6-(bromomethyl)-4-phenyl-1,3-oxazinan-2-one 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 4383-23-7 (S)-1-phenylbut-3-en-1-amine 
• 135865-77-9 (S)-N-(tert-Butoxycarbonyl)-1-phenyl-3-butenylamine 

Downstream Products

• 385435-12-1 (S)-9-Phenyl-1,4-dithia-8-aza-spiro[4.5]decan-7-one 
• 1026470-49-4 Trifluoro-acetic acid (2S,4R)-2-phenyl-1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl ester 
• 259856-87-6 (2S,4R)-(-)-4-Acetoxy-2-phenyl-1-trifluoroacetylpiperidine 
• 259856-83-2 (2S,4R)-(-)-2-Phenylpiperidine-4-ol 
• 326477-55-8 (4S,6S)-(-)-4-Hydroxy-6-phenylpiperidin-2-one 

Relevant academic research and scientific papers

A new method of synthesis of 6-substituted piperidine-2,4-diones from homoallylamines

Mono- and dihomoallylamines serve as convenient precursors for the preparation of 6-substituted piperidine-2,4-diones. This transformation is based, on the one hand, on a simple and well-known halocyclocarbamation reaction proceeding by the addition of a

Addition of dienolates to sulfinimines. Stereoselective synthesis of dihydropyridones

The vinylogous Mannich reaction of sulfinimines with dienolates was investigated. Lithium and trimethylsilyl enolates of ethyl 3-ethoxycrotonate reacted with enantiopure 10-isobornylsulfinimines to give derivatives of δ-aminoacids which were cyclised to 6-aryl substituted derivatives of 2(1H)-pyridinones. 6-Aryl substituted 2,4-piperidinediones with either (S) or (R) configuration were analogously obtained using lithium and TMS enolates of 2,2,6-trimethyl-1,3-dioxin-4-one.

Asymmetric synthesis of the four stereoisomers of 4-hydroxypipecolic acid

The asymmetric synthesis of all four stereoisomers of 4-hydroxypipecolic acid (1) from the polyfunctionalized chiral building blocks δ-amino β-keto esters (S(S),R)-(+)-5 or (R(S),S)-(-)-5 is described. Key steps in the synthesis are the stereoselective reductions of b-phenylpiperidine-2,4-dione (6) and N-sulfinyl δ-amino β-keto esters 5 to cis 4-hydroxy 2-piperidinone 7 and syn-δ-amino β-hydroxy ester 9, respectively. The only protecting/deprotecting group chemistry required is related to the oxidation step.