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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 59, Number 1
JKCSEZ 59(1)
February 20, 2015 

Diastereoselective Reduction of 2,3-Dioxo-4-carboxy-5-substituted Pyrrolidines Using NaBH4/AcOH and Heterogenous Hydrogenation Reactions
Mohd Fazli Mohammat, Nurul Shulehaf Mansor, Zurina Shaameri, Ahmad Sazali Hamzah*
2,3-Dioxo-pyrrolidine, Diastereoselective, Enol reduction
Diastereoselective reduction of 2,3-dioxo-4-carboxy-5-(substituted)pyrrolidine 1 by NaBH4/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.
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