209160-37-2

Upstream product

• 209160-33-8 (+)-(2S,5S,6R)-1-aza-2-(3-furyl)-5-methyl-8-oxa-4,9-dioxobicyclo[4.3.0]nonane 
• 181528-70-1 (2R,3S,6S)-6-Furan-3-yl-2-hydroxymethyl-3-methyl-piperidin-4-one 
• 100-39-0 benzyl bromide 
• 209160-35-0 (-)-(2S,4R,5S,6R)-1-aza-2-(3-furyl)-4-hydroxy-5-methyl-8-oxa-9-oxobicyclo[4.3.0]nonane 

Downstream Products

• 209160-47-4 (5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid 
• 209160-55-4 (5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The α-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the α-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.