• Title/Summary/Keyword: 2,3-Dioxo-pyrrolidine

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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
    • Journal of the Korean Chemical Society
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    • v.59 no.1
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    • pp.31-35
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    • 2015

  • 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.

  • https://doi.org/10.5012/jkcs.2015.59.1.31 인용 PDF KSCI KPUBS HTML

[$(3aR^*,6aS^*)$-6a-Hydroxy-Asymmetric Synthesis of cyclopenta[b]pyrrole-3a-carboxylate and Determination of Its Stereostructure via NMR Spectrum ($(3aR^*,6aS^*)$-6a-Hydroxy-cyclopenta[b]pyrrole-3a-carboxylate의 부제합성 및 NMR 스텍트럼을 통한 입체구조의 결정)

  • Kwon, Soon-Kyoung;Park, Myoung-Suk;Seo, Won-Jun
    • YAKHAK HOEJI
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    • v.38 no.5
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    • pp.544-554
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    • 1994

  • Pyrrolidine-2,3-dione derivative A was synthesized from oxalylation of chiral enamine Ba. The stereostructure of its major diastereomer $(A_{maj})$ was determined as octahydro-2,3-dioxo-6aS-hyd roxy-1-(1S-methoxycarbonyl-2-phenylethyl)-cyclopenta[b]pyrrole-3aR-carboxylic acid ethyl ester Aa by means of NMR spectrum. This result implied that the asymmetric carbon-carbon bond forming reaction occurred preferentially at the ${\beta}-face$ of Ba.

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