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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 23
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Original Articles

Lutetium Triflate as an Efficient and Recyclable Catalyst for Chemoselective Thioacetalization of Aldehydes

Pages 4401-4408 | Received 30 Jul 2004, Published online: 12 Jan 2011

References

  • Greene , T. W. and Wuts , P. G.M. 1999 . Protective Groups in Organic Synthesis 329 New York : Wiley .
  • Seebach , D. 1969 . Methods and Possibilities of Nucleophilic Acylation . Angew. Chem., Int. Engl. , 8 : 638
  • Grobel , B. T. and Seebach , D. 1977 . Umpolung of the Reactivity of Carbonyl Compounds Through Sulfur Containing Reagents . Synthesis , : 357 [CROSSREF]
  • Bulman Page , P. C. , Van Niel , M. B. and Prodger , J. C. 1989 . Synthetic Uses of the 1,3‐Dithiane Grouping from 1977 to 1988 . Tetrahedron , 45 : 7643 [CROSSREF]
  • Pettit , G. R. and Tamelen , E. E. 1962 . Org. React. , 12 : 356
  • Djerassi , C. and Gorman , M. 1953 . Studies in Organic Sulfur Compounds, VI, Cyclic Ethylene and Trimethylene Hemiketals . J. Am. Chem. Soc. , 75 : 3704
  • Wilson , G. E. , Huang , M. G. and Schloman , W. W. 1968 . Facile Synthesis of 1,3‐Oxathiolanes from Ketones and Mercaptoethanol . J. Org. Chem. , 33 : 2133
  • Nakata , T. , Nagao , S. , Mori , S. and Oishi , T. 1985 . Tetrahedron Lett. , 26 : 6461 [CROSSREF]
  • Corey , E. J. and Shimoji , K. 1983 . Magnesium and Zinc‐Catalyzed Thioketalization . Tetrahedron Lett. , 24 : 169 [CROSSREF]
  • Burezyk , B. and Kortylewicz , Z. 1982 . Organic Sulfur Compounds; II, Sulfur Dioxide as Catalyst in the Synthesis of Thioacetals from Aldehydes or Ketones and Alkanethiols, Alkanedithiols or Hydroxyalkanethiols . Synthesis , : 831 [CROSSREF]
  • Ravindranathan , T. , Chavan , S. P. and Dante , S. D. 1995 . Interconversion of Oxathiolanes and Carbonyls under Essentially Identical Conditions . Tetrahedron Lett. , 36 : 2285 [CROSSREF]
  • Ong , B. S. 1980 . A Simple and Efficient Method of Thioacetal and Ketalization . Tetrahedron Lett. , 21 : 4225 [CROSSREF]
  • Kumar , V. and Dev , S. 1983 . Titanium Tetrachloride, an Efficient and Convenient Reagent for Thioacetalization . Tetrahedron Lett. , 24 : 1289 [CROSSREF]
  • Anand , R. V. , Sarvanan , P. and Singh , V. K. 1999 . Solvent Free Thioacetalization of Carbonyl Compounds Catalyzed by Cu(OTf)2‐SiO2 . Synlett. , : 415
  • Kamitori , Y. , Hojo , M. , Mashuda , R. , Kamura , T. and Yoshida , J. 1986 . Selective Protection of Carbonyl Compounds, Silica Get Treated with Thionyl Chloride as an Effective Catalyst for Thioacetalization . J. Org. Chem. , 52 : 4665
  • Karimi , B. and Seradj , H. 2000 . Zirconium Tetrachloride as an Efficient and Chemoselective Catalyst for Conversion of Carbonyl Compounds to 1,3‐Oxathiolanes . Synlett. , : 805
  • Madhuswamy , S. , Arulananda , S. and Gunanatham , C. 2001 . Indium(III) Chloride as an Efficient, Convenient Catalyst for Thioacetalization and its Chemoselectivity . Tetrahedron Lett. , 42 : 359 [CROSSREF]
  • Samajdar , S. , Basu , M. K. , Becker , F. F. and Banik , B. K. 2001 . A New Molecular Iodine Catalyzed Thioacetalization of Carbonyl Compounds: Selectivity and Scope . Tetrahedron Lett. , 42 : 4425 [CROSSREF]
  • Vaino , A. R. and Szarek , W. A. 1996 . J. Chem. Soc., Chem. Commun. , : 2351
  • Firouzabadi , H. , Iranpoor , N. and Karimi , B. 1999 . Lithium Bromide‐Catalyzed Highly Chemoselective and Efficient Dithioacetalization of α,β‐Unsaturated and Aromatic Aldehydes under Solvent‐Free Conditions . Synthesis , : 58 [CROSSREF]
  • Tandon , M. and Begley , T. P. 1997 . Synth. Commun. , 27 : 2953
  • Jadav , J. S. , Reddy , B. V. and Pandey , S. K. 2001 . LiBr4 Catalyzed Chemoselective Conversion of Aldehydes to 1,3‐Oxathiolanes and 1,3‐Dithianes . Synlett. , : 238
  • Metcalf , B. W. , Burkhart , J. P. and Jund , K. 1980 . Cleavage of tert‐Butyldimethylsilyl Ethers by Tetrafluoroborate Salt . Tetrahedron Lett. , 21 : 35 [CROSSREF]
  • Kamal , A. and Chouhan , G. 2002 . Scandium Triflate as a Recyclable Catalyst for Chemoselective Thioacetalization . Tetrahedron Lett. , 43 : 1347 [CROSSREF]
  • Saraswathy , V. G. , Geetha , V. and Sankaranan , S. S. 1994 . Chemoselective Protection Aldehyde as Dithioacetals in Lithium Perchlorate Diethyl Ether Medium. Evidence for the Formation of Oxocarbenium Ion Intermediate from Acetals . J. Org. Chem. , 52 : 4665
  • Kobayashi , S. 1999 . Scandium Triflate in Organic Synthesis . Eur. J. Org. Chem. , : 15 [CROSSREF]
  • Kobayashi , S. 1994 . Rare Earth Metal Trifluromethanesulfonate as Water‐Tolerant Lewis Acid Catalysts in Organic Synthesis . Synlett. , : 689 [CROSSREF]
  • Kamitori , Y. , Hojo , M. , Masuda , R. , Kimura , T. and Yoshida , T. 1986 . Selective Protection of Carbonyl Compounds . J. Org. Chem. , 51 : 1427
  • Degani , I. and Regondi , R. 1981 . Mercury(II) Oxide/35% Aqueous Tetrafluoroboric Acid/Tetrahydrofuran . Synthesis , : 51 [CROSSREF]
  • Gonnela , N. C. , Lakshmikanta , M. V. and Cava , M. P. 1979 . A New Synthesis of Aromatic Dithio Esters . Synth. Commun. , 9 : 17
  • Prabhat , A. , Samson , S. , Leasge , M. and Goiller , D. 1990 . Tris(trimethylsilyl)silane (TTMSS): Formation of Carbon‐Centered Radicals from 1,3‐Dithiolanes and 1,3‐Dithianes . J. Org. Chem. , 55 : 6248

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