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http://dx.doi.org/10.5012/jkcs.2015.59.1.31

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

Mohammat, Mohd Fazli (Organic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA)
Mansor, Nurul Shulehaf (Department of Chemistry, Universiti Teknologi MARA)
Shaameri, Zurina (Organic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA)
Hamzah, Ahmad Sazali (Organic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA)
Publication Information
Journal of the Korean Chemical Society / v.59, no.1, 2015 , pp. 31-35 More about this Journal
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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1 Southwick, P. L.; Previc, E. P.; Casanova, J.; Carlson, E. H. J. Org. Chem. 1956, 21, 1087-1095.   DOI
2 (a) Mohammat, M. F.; Najim, N.; Mansor, N. S.; Sarman, S.; Shaameri, Z.; Mat Zain, M.; Hamzah, A. S. ARKIVOC 2011, ix 429-438.
3 Frage, C. A. M.; Barreiro, E. J.; Synth. Commun. 1995, 25, 1133.   DOI
4 Metten, B.; Kostermans, M.; Van Baelen, G.; Smet, M.; Dehaen, W. Tetrahedron 2006, 62, 6018-6028.   DOI
5 Iglesias, M. J. Org. Chem. 2003, 68, 2680-2688.   DOI
6 Besson, M.; Pinel, C. Top. Catal. 2003, 25, 43-61.   DOI
7 Royles, B. J. L. Chem. Rev. 1995, 95, 1981-2001.   DOI
8 (a) Page, P. C. B.; Hamzah, A. S.; Leach, D. C.; Allin, S. M.; Andrews, D. M.; Rassias, G. A. Org. Lett. 2003, 5, 353.   DOI
9 Li, J.; Liu, S.; Niu, S.; Zhuang, W.; Che, Y. J. Nat. Prod. 2009, 72, 2184-2187.   DOI
10 Endo, A.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 8298-8299.   DOI
11 (a) Jourdan, F.; Kaiser, J. T.; Lowe, D. J. Synth. Commun. 2003, 33, 2235−2241.   DOI
12 Bender, D. R.; Bjeldanes, L. F.; Knapp D. R.; Rapoport, H. J. Org. Chem. 1975, 40, 1264-1269.   DOI
13 Dasse, O. A.; Evans, J. L.; Zhai, H.; Zou, X. D.; Kintigh, J. T. Lett. Drug. Des. Discov. 2007, 4, 263-271.   DOI
14 Mansor, N. S.; Mohammat, M. F.; Shaameri, Z.; Khaledi, H. Acta. Cryst. E. 2013, E69, 293-294.