869468-01-9

Upstream product

• 869468-00-8 E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-hex-2-enamide 
• 103-49-1 dibenzylamine 
• 90-82-4 pseudoephedrine 
• 97943-16-3 (E)-2-hexenoyl chloride 
• 958637-76-8 (+)-(1'S,2'S,2E)-N-(2'-tert-butyldimethylsilyloxy-1'-methylethyl-2'-phenyl)-N-methylhex-2-enamide 
• 85175-35-5 lithium dibenzylamide 

Downstream Products

• 869468-29-1 (+)-(1'S,2'S,3R)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)hexanamide 

Relevant academic research and scientific papers

A general and enantiodivergent method for the asymmetric synthesis of piperidine alkaloids: concise synthesis of (R)-pipecoline, (S)-coniine and other 2-alkylpiperidines

A simple and very efficient protocol for the preparation of highly enantioenriched 2-alkylpiperidines has been set up, which allows the preparation of the final heterocycles with any wanted configuration at the stereogenic center starting from the same starting material. The key step of the synthesis relies on a diastereodivergent aza-Michael reaction protocol using the readily available and cheap reagent (+)-(S,S)-pseudoephedrine as chiral auxiliary.

(S,S)-(+)-pseudoephedrine as chiral auxiliary in asymmetric aza-Michael reactions. Unexpected selectivity change when manipulating the structure of the auxiliary

The asymmetric aza-Michael reaction of metal benzylamides to α,β-unsaturated amides derived from the chiral amino alcohol (S,S)-(+)-pseudoephedrine has been studied in detail. A deep study of the most important experimental parameters (solvent, temperatur