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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 5
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Original Articles

Convenient Preparation of Benzylseleno‐ and Phenylselenoalkanoic Acids: Reagents for Synthesis of Organoselenium Compounds

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Pages 783-793 | Received 24 Jul 2006, Published online: 10 Mar 2007

References

  • Tanaka , J. 1995 . Selenium: Physiological and pharmacological roles of selenocompounds . Kikan Kagaku Sosetsu , 27 : 120 – 131 . Chem. Abstr. 1996, 124, 338600
  • Masukawa , T. 1987 . The Chemistry of Organic Selenium and Tellurium Compounds Edited by: Patai , S. Vol. 2 , Chichester : John Wiley & Sons . Chap. 9
  • Schwarz , K. and Foltz , C. M. 1957 . Selenium as an integral part of factor 3 against dietary necrotic liver degeneration . J. Am. Chem. Soc. , 79 : 3292 – 3293 .
  • Klayman , D. L. 1973 . Organic Selenium Compounds Edited by: Gunther , W. H. New York : Wiley‐Interscience .
  • Clive , D. L. J. 1978 . Modern organoselenium chemistry . Tetrahedron , 34 : 1049 – 1132 .
  • Lucas , M. A. , Nguyen , O. T. K. , Schiesser , C. H. and Zhend , S. L. 2000 . Preparation of 5‐selenopentopyranose sugars from pentose starting materials by samarium (II) iodide or (phenylseleno) formate mediated ring closures . Tetrahedron , 56 : 3995 – 4000 .
  • Al‐Maharik , N. , Engman , L. , Malmström , J. and Schiesser , C. H. 2001 . Intramolecular homolytic substitution at selenium: Synthesis of novel selenium‐containing vitamin E analogues . J. Org. Chem. , 66 : 6286 – 6290 .
  • Burnett , D. A. , Caplen , M. A. , Davis , H. R. Jr. , Burrir , R. E. and Clader , J. W. 1994 . 2‐Azetidinones as inhibitors of cholesterol absorption . J. Med. Chem. , 37 : 1733 – 1736 .
  • Skiles , J. W. and McNeil , D. 1990 . Spiro indolinone beta‐lactams, inhibitors of poliovirus and rhinovirus 3C‐ proteinases . Tetrahedron Lett. , 31 : 7277 – 7280 .
  • Smith , D. M. , Kazi , A. , Smith , L. , Long , T. E. , Heldreth , B. , Turos , E. and Dou , Q. P. 2002 . A novel β‐lactam antibiotic activates tumor cell apoptotic program by inducing DNA damage . Mol. Pharmacol. , 61 : 1348 – 1358 .
  • Madan , S. , Arora , R. , Venugopalan , P. and Bari , S. S. 2000 . A new synthetic approach for novel C‐3 substituted β‐lactams . Tetrahedron Lett. , 41 : 5577 – 5581 .
  • Bari , S. S. , Venugopalan , P. and Arora , R. 2003 . A facile Lewis acid–promoted allylation of azetidin‐2‐ones . Tetrahedron Lett. , 44 : 895 – 897 .
  • Bari , S. S. , Venugopalan , P. , Arora , R. , Modi , G. and Madan , S. 2006 . An unusual Lewis acid promoted isomerization of trans‐3‐halophenylthio‐β‐lactams . Heterocycles , 68 : 749 – 762 .
  • Bhalla , A. , Madan , S. , Venugopalan , P. and Bari , S. S. 2006 . C‐3 β‐Lactam carbocation equivalents: Versatile synthons for C‐3 substituted β‐lactams . Tetrahedron , 62 : 5054 – 5063 .
  • Bhalla , A. , Rathee , S. , Madan , S. , Venugopalan , P. and Bari , S. S. 2006 . Lewis acid mediated functionalization of β‐lactams: Mechanistic study and synthesis of C‐3 unsymmetrically disubstituted azetidin‐2‐ones . Tetrahedron Lett. , 47 : 5255 – 5259 .
  • Bhalla , A. , Venugopalan , P. and Bari , S. S. 2006 . Facile stereoselective synthesis of cis‐ and trans‐3‐alkoxyazetidin‐2‐ones . Tetrahedron , 62 : 8291 – 8302 .
  • Carland , M. W. and Schiesser , C. H. 2004 . Preparation of novel selenopenams by intramolecular homolytic substitution . Molecules , 9 : 466 – 471 .
  • Fredga , A. 1974 . Some benzylseleno‐ and β‐phenylethylseleno‐substituted alkanoic acids . Acta Chem. Scand. B , 28 : 692 – 694 .
  • Benjamin , L. J. , Schiesser , C. H. and Sutej , K. 1993 . Homolytic substitution at selenium: ring closure of ω‐(benzylseleno)alkyl radicals . Tetrahedron , 49 : 2557 – 2566 .
  • Liu , Y. K. and Zhang , Y. M. 2000 . Synthesis of β‐aminoesters α‐selenoesters via active metal bismuth produced by Sm/BiCl3 system in aqueous media . Chin. Chem. Lett. , 11 : 195 – 198 .
  • Sharpless , K. B. and Lauer , R. F. J. 1973 . A mild procedure for the conversion of epoxides to allylic alcohols: The first organoselenium reagent . J. Am. Chem. Soc. , 95 : 2697 – 2699 .

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