326477-46-7

Upstream product

• 267011-72-3 methyl (S_S,R)-(+)-methyl 3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate 

Downstream Products

• 620158-91-0 (S_S,1R,3R)-(+)-1-phenyl-1-N-(p-toluenesulfinyl)amino-3-hydroxy-5-oxo-hexane 
• 620158-92-1 (2R,4R)-6-Methyl-2-phenyl-2,3,4,5-tetrahydro-pyridin-4-ol 
• 620158-90-9 (S_S,3R,5R)-(+)-3-hydroxy-5-phenyl-5-N-(p-toluenesulfinyl)aminopentanoic acid N-methoxy-N-methylamide 

Relevant academic research and scientific papers

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.