Concise Enantioselective Synthesis of Naturally Active (S)-3-Hydroxypiperidine |
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| Authors: | Soumen Dey Pratibha U Karabal |
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| Institution: | Chemical Engineering and Process Development Division, CSIR–National Chemical Laboratory, Pune, India |
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| Abstract: | 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%). |
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| Keywords: | Asymmetric synthesis bioactivity enantioselectivity natural products organocatalysis |
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