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Diastereoselective Reduction of 2,3-Dioxo-4-carboxy-5-substituted Pyrrolidines Using NaBH4/AcOH and Heterogenous Hydrogenation Reactions

  • Mohammat, Mohd Fazli ;
  • Mansor, Nurul Shulehaf ;
  • Shaameri, Zurina ;
  • Hamzah, Ahmad Sazali
  • Received : 2014.11.19
  • Accepted : 2014.12.11
  • Published : 2015.02.20

Abstract

Diastereoselective reduction of 2,3-dioxo-4-carboxy-5-(substituted)pyrrolidine 1 by $NaBH_4/AcOH$ and heterogenous hydrogenation were reported. Stereochemical assignment and diastereomeric ratios of the products were determined using $^1H$ NMR and single crystal X-ray analyses. The steric factors of the C-5 substituents of the pyrrolidinone was shown to have an interesting influence on both the yield and diastereoselectivity of the reduced product.

Keywords

2,3-Dioxo-pyrrolidine;Diastereoselective;Enol reduction

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