190383-55-2Relevant academic research and scientific papers
A new synthesis of all four stereoisomers of 2-(2,3- dihydroxypropyl)piperidine via iterative asymmetric dihydroxylation to cause enantiomeric enhancement. Application to asymmetric synthesis of naturally occurring piperidine-related alkaloids
Takahata, Hiroki,Kubota, Minoru,Ikota, Nobuo
, p. 8594 - 8601 (2007/10/03)
Both enantiomers of 2-(2-propenyl)piperidine 1 (76-88% ee), prepared via the first asymmetric dihydroxylation (AD) of 5-hexenyl azide, underwent the second AD to provide all four of the stereoisomeric 2-(2,3- dihydroxypropyl)piperidines 2 with enantiomeric enhancement.(>98% ee). An asymmetric synthesis, starting from 2, of several 2-(2- hydroxyalkyl)piperidine alkaloids [(-)halosaline, (+)-N-methylallosedridine, (+)-8-ethylnorlobelol, (+)-sedridine, (+)-allosedridine, (-)allosedridine, and (+)-N-methylsedridine] and the ant defense alkaloids [(+)-tetraponerine-3 (T-3), T-4, T-7, and T-8] is demonstrated.
A general entry to 2-(2-hydroxyalkyl)piperidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement
Takahata, Hiroki,Kubota, Minoru,Momose, Takefumi
, p. 3451 - 3454 (2007/10/03)
Both enantiomers of 2-(2-propenyl)piperidine (1) (76-88% ee), prepared via the first AD of 5-hexenyl azide, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)piperidines (2) with enantiomeric enhancement (>98 ee). An asy
