181528-77-8

Upstream product

• 181528-69-8 (S)-1-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-1-methylene-but-2-enyl]-2-methoxymethyl-pyrrolidine 
• 121693-79-6 (E)-tert-butyldimethyl-((3-methylpent-2-en-4-yn-1-yl)oxy)silane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 181783-40-4 (-)-(2R,3S,6S)-2-hydroxymethyl-3-methyl-6-phenyl-4-piperidone 
• 181783-49-3 (2R,3R,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-6-phenyl-piperidin-4-one 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 

Downstream Products

• 181783-40-4 (-)-(2R,3S,6S)-2-hydroxymethyl-3-methyl-6-phenyl-4-piperidone 
• 181783-53-9 (2R,3S,4R,6S)-1-aza-4-hydroxy-3-methyl-6-phenyl-8-oxa-7-oxobicyclo[4.3.0]nonane 
• 181783-52-8 (2R,3S,6S)-1-aza-3-methyl-6-phenyl-8-oxa-4,7-dioxobicyclo[4.3.0]nonane 
• 209160-23-6 (2R,3S,6S)-3-Methyl-4-oxo-6-phenyl-piperidine-1,2-dicarboxylic acid 2-methyl ester 1-(2,2,2-trichloro-ethyl) ester 
• 209160-21-4 (2R,3S,6S)-2-Hydroxymethyl-3-methyl-4-oxo-6-phenyl-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 209160-19-0 (2R,3S,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-4-oxo-6-phenyl-piperidine-1-carboxylic acid 2,2,2-trichloro-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.

Enantioselective Synthesis of HIghly Functionalized 4-PIperidones by the Asymmetric Imino-Diels-Alder Reaction of Chiral 2-Amino-1,3-butadienes

Chiral 2-amino-1,3-butadienes 1 derived from commercially available (S)-2-methoxymethylpyrrolidine react with aromatic N-trimethylsilyaldimines and N-phenylaldimines in the presence of ZnCl2 to give, after reaction workup, 4-piperidones 4 and 6, respectively, with moderate to very high enantiomeric excesses.In addition, the absolute configurations of derivatives of 4a and 4g were determined by circular dichroism and NMR spectroscopy on the Mosher ester, respectively. - Keywords: asymmetric Diels-Alder reactions; butadienes; Diels-Alder reactions; piperidones