Enantioselective synthesis of 3-hydroxypiperidin-2-ones

  • Gibbs G
  • Hateley M
  • McLaren L
 et al. 
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Abstract

An efficient synthesis of (S)- and (R)-3-hydroxypiperidin-2-ones from methyl 5-nitro-2-oxopentanoate is described. A one-pot enzyme catalysed hydrolysis of the ester and reduction of the ketone gave enantiopure 2- hydroxy-5-nitropentanoic acids which on esterification, catalytic hydrogenation over a platinum(IV) oxide catalyst and intramolecular: cyclisation gave the target compounds in 93% overall yield and >99% ee.

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Authors

  • Gary Gibbs

  • Martin J. Hateley

  • Lee McLaren

  • Matthew Welham

  • Christine L. Willis

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