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Mukaiyama Reagent: Novel One-Pot System for the Synthesis of 1,3-Oxathiolan-5-one

Author Affiliations

  • 1Department of Chemistry, Government Vidarbha Institute of Science and Humanities, Amravati, MS, India
  • 2Department of Chemistry, Government Vidarbha Institute of Science and Humanities, Amravati, MS, India

Res.J.chem.sci., Volume 6, Issue (10), Pages 8-12, October,18 (2016)


A new application of mukaiyama reagent for the simple conversion of aldehyde and mercaptoacetic acid into the corresponding 1,3-oxathiolan-5-one is described. The transformation can be achieved in DMF and the method provides rapid and easy access to 1,3-oxathiolan-5-one compounds in good to excellent yields without any chromatographic purification.


  1. Popp A., Gilch A., Mersier A.L., Peterson H., Mechlem J.R. and Stohrer. (2004)., Enzymatic kinetic resolution of 1,3-dioxolan-4-one and 1,3-oxathiolan-4-one derivatives: Synthesis of key intermediate in the industrial synthesis of the nucleoside reverse transcriptase inhibitor AMDOXOVIOR., J. Adv. Synth. Catal., 346(6), 682-690.
  2. Choi W.S., Wilson L.J., Yeola S., Lotta D.C. and Schinazi R.F. (1991)., In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of thialanyl and dioxolanyl nucleoside analogs., J. Am. Chem. Soc., 113(24), 9377-9379.
  3. Lotta D.C., Schinazi R.F. and Choi W.S. (1992)., Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane., Emory University, USA, WO 9214743 A2.
  4. Lotta D.C. and Choi W.S. (1991)., Method and compositions for the synthesis of BCH-189 and related compounds., Emory University, USA, WO 9111186 A1.
  5. Nguyen B.N., Lee N., Chan L. and Zacharie B. (2003)., Synthesis and antiviral activities of N-9-oxypurine 1,3-dioxolane and 1,3-oxathiolane nucleosides., Biorg. Med. Chem. Lett., 10(19), 2223-2226.
  6. Rajopadhye M. and Popp F.D. (1988)., Potential anticonvulsants. 11. Synthesis and anticonvulsant activity of spiro[1,3-dioxolane-2,3’-indolin]-2’-ones and structural analogs., J. Med. Chem., 31(5), 1001-1005.
  7. Aloup J.C., Bouchaudon J., Farge D., Deregnaucourt J. and Hardy M.H. (1987)., Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide., J. Med. Chem., 30(1), 24-29.
  8. Miyauchi H., Tanio T. and Ohashi N. (1996)., Synthesis and antifungal activity of new azole derivatives containing an oxathiane ring., Biorg. Med. Chem. Lett., 6(20), 2377-2380.
  9. Nokami J., Ryokume K. and Inada J. (1995)., Synthesis of 1,3-oxathialane derivatives as novel precursors of 2’,3’-dideoxy-3’-oxa-4’-thioribonucleosides., Tetrahedron Lett., 36(34), 6099-6100.
  10. Fisher A., Brandeis R., Pittel Z., Karton I., Sapir M., Dachir S., Levy A. and Heldman E. (1989)., (±)-cis-2-methyl-spiro(1,3-oxathiolane-5,3’)quinuclidine (AF102B): A new M1 agonist attenuates cognitive dysfunctions in AF64A-treated rats., Neurosci. Lett., 102(2-3), 325-331.
  11. Dei S., Bellucci C., Muccioni M., Ferraroni M., Gundalini L., Manetti D., Marucci G., Maticci R., Nesi M., Romanelli M.N., Scapechi S. and Teodori E. (2008)., Muscarinic antagonists with multiple stereocenters: synthesis, affinity profile and functional activity of isomeric 1-methyl-2-(2,2-alkylaryl-1,3-oxthiolan-5-yl)pyrrolidine sulfoxide derivatives., Bioorg. Med. Chem., 16(10), 5490-5500.
  12. Angeli P., Brasili L., Gianella M., Gualtieri F., Picchio M.T. and Teodori E. (1988)., Chiral muscarinic agonists possessing 1 1,3-oxatholane nucleus: enantio- and tissue-selectivity on isolated preparations of guinea-pig ileum and atria and of rat urinary bladder., Naunyn-Schmiedeberg’s Arch. Pharmacol., 337(3), 241-245.
  13. Pilgram K.H.G. (1977)., Herbicidal heterocyclic compounds., US Pat. Appl. US 4019892.
  14. Krumkalna E.V. (1981)., Methods for plant growth regulation., US Pat. Appl. US 4282030.
  15. Higashiya S., Narizuka S., Konno A., Maeda T., Momota K. and Fuchigami T. (1999)., Electrolytic partial fluorination of organic compounds. Drastic improvement of anodic monofluorination of 2-substituted -1,3-oxathiolan-5-ones., J. Org. Chem., 64(1), 133-137.
  16. Uang B.J., Po S.Y., Hung S.C., Liu H.H., Hsu C.Y., Lin Y.S. and Chang J. (1997)., Asymetric-synthesis employing chiral ketones as templates., W. Pure Appl. Chem., 69(3), 615-620.
  17. Pustovit Y.M., Alekseenko A.N., Subota A.I. and Tolmachev A.A. (2006)., Convenient method for the synthesis of 2-trifluoromethyl-1,3-oxathiolan-5-ones., Chem. Heterocycl. Compd., 42(2), 278-279.
  18. Yadav L.D.S., Yadav S. and Rai V. K. (2005)., A highly efficient green catalytic system for one pot synthesis of 1,3-oxathiolan-5-ones., Tetrahedron, 61(20), 10013.
  19. Shibata I., Baba A., Iwaski H. and Matsuda H. (1986)., Cycloaddition reaction of heterocumulenes with oxiranes catalysed by organotin iodide-lewis base complex., J. Org. Chem., 51(12), 2177-2184.
  20. Dewan M., Kumar A., Saxena A., De A. and Mozumdar M. (2010)., Molecular iodine in [bmim][BF4]: a highly efficient green catalytic system for one pot synthesis of 1,3-oxathiolan-5-one., Tetrahedron Lett., 51(47), 6108-6118.
  21. Nagashoma T., Lu Y., Petro M.J. and Zhang W. (2005)., Fluorous 2-chloropyridinium salt (Mukaiyama condensation reagent) for amide formation reactions., Tetrahedron letters, 46(38), 6585-6588.
  22. Matsugi M., Hasegawa M., Sadachika D., Okamato S., Tomioka M., Ikeya Y., Masuyama A. and Mori Y. (2007)., Preparation and condensation reactions of a new light-fluorous Mukaiyama reagent: reliable purification with fluorous solid phase extraction for esters and amides., Tetrahedron Lett., 48(23), 4147-4150.
  23. Mukaiyama T. (1979)., New synthetic methods based on the onium satls of aza-arenes., Angew. Chem. Int. Ed., 18, 707