Synthetic Communications p. 1559 - 1565 (2015)
Update date:2022-07-30
Topics: Synthesis Enantiomer Chiral Enantioselective Chemical reactions Experimental Concise 3-Hydroxypiperidine Naturally active
Dey, Soumen
Karabal, Pratibha U.
Sudalai, Arumugam
A short and efficient enantioselective synthesis of natural product (S)-3-hydroxypiperidine has been achieved starting from commercially available raw materials employing two catalytic routes: (i) cocatalyzed hydrolytic kinetic resolution (HKR) of racemic methyl-3-(oxiran-2-yl)propanoate; (ii) proline-catalyzed α-aminooxylation followed by Horner-Wardsworth-Emmons olefination in high enantiomeric purity (97% ee) and high overall yield (38%). (Chemical Equation Presented).
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