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

대한화학회지 2015년 59권 1호 p.31 ~ 35
 ( Mohammat Mohd Fazli ) - Universiti Teknologi MARA Institute of Science

 ( Mansor Nurul Shulehaf ) - Universiti Teknologi MARA Department of Chemistry
 ( Shaameri Zurina ) - Universiti Teknologi MARA Institute of Science
 ( Hamzah Ahmad Sazali ) - Universiti Teknologi MARA Institute of Science

Abstract


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.

키워드

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