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Synthesis 2010(6): 1023-1029  
DOI: 10.1055/s-0029-1218640
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of New Enantiomerically Pure Organoiodine Catalysts and Their Application in the α-Functionalization of Ketones

Umar Farooqa,b, Sascha Schäfera, Azhar-ul-Haq Ali Shaha,c, Diana Maria Freudendahla, Thomas Wirth*a
a Cardiff University, School of Chemistry, Main Building, Park Place, Cardiff CF10 3AT, UK
Fax: +44(29)20876968; e-Mail: wirth@cf.ac.uk;
b COMSATS Institute of Information Technology, Abbottabad, Pakistan
c Kohat University of Science and Technology, Kohat, Pakistan
Further Information

Publication History

Received 29 September 2009
Publication Date:
08 January 2010 (online)

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Abstract

The synthesis of enantiomerically pure iodoarenes and their application to the α-oxysulfonylation of propiophenone, and the lactonization of 5-oxo-5-phenylpentanoic acid using MCPBA as stoichiometric oxidant are reported to give useful synthetic intermediates in good yields and moderate enantioselectivities.

Key words

hypervalent iodine reagents - organocatalysis - oxidation - stereoselective synthesis

    References

  • Reviews:
  • 1a Varvoglis A. The Organic Chemistry of Polycoordinated Iodine   VCH; Weinheim: 1992. 
  • 1b Varvoglis A. Hypervalent Iodine in Organic Synthesis   Academic Press; London: 1997. 
  • 1c Finet J. Ligand Coupling Reactions with Heteroatomic Compounds   Pergamon; Oxford: 1998. 
  • 1d Zhdankin VV. Stang PJ. Tetrahedron  1998,  55:  10927 
    Search in Google Scholar
  • 1e Wirth T. Hirt UH. Synthesis  1999,  1271 
  • 1f Ochiai M. In Chemistry of Hypervalent Compounds   Akiba K. VCH; New York: 1999.  p.359 
  • 1g Zhdankin VV. Stang PJ. Chem. Rev.  2002,  102:  2523 
    Search in Google Scholar
  • 1h Wirth T. Hypervalent Iodine Chemistry   Springer; Berlin: 2003. 
  • 1i Tohma H. Kita Y. Adv. Synth. Catal.  2004,  346:  111 
    Search in Google Scholar
  • 1j Wirth T. Angew. Chem. Int. Ed.  2005,  44:  3656 ; Angew. Chem. 2005, 117: 3722
    Search in Google Scholar
  • 1k Zhdankin VV. In Science of Synthesis   Vol. 31a:  Ramsden C. Thieme; Stuttgart: 2007.  Chap. 31.4.1. p.161 
    Search in Google Scholar
  • 1l Zhdankin VV. Stang PJ. Chem. Rev.  2008,  108:  5299 
    Search in Google Scholar
  • 2 Braddock DC. Cansell G. Hermitage SA. Chem. Commun.  2006,  2483 
    Crossref
  • 3 Rebrovic L. Koser GF. J. Org. Chem.  1984,  49:  2462 
    CrossrefSearch in Google Scholar
  • 4 Koser GF. Relenyi AG. Kalos AN. Rebrovic L. Wettach RH. J. Org. Chem.  1982,  47:  2487 
    CrossrefSearch in Google Scholar
  • 5a Altermann SM. Richardson RD. Page TK. Schmidt RK. Holland E. Mohammed U. Paradine SM. French AN. Richter C. Bahar AM. Witulski B. Wirth T. Eur. J. Org. Chem.  2008,  5315 
  • 5b Shah AA. Khan ZA. Choudhary N. Lohölter C. Schäfer S. Marie GPL. Farooq U. Witulski B. Wirth T. Org. Lett.  2009,  11:  3578 
    Search in Google Scholar
  • 6a Wirth T. Hirt U. Tetrahedron: Asymmetry  1997,  8:  23 
    Search in Google Scholar
  • 6b Hirt UH. Springler B. Wirth T. J. Org. Chem.  1998,  63:  7674 
    Search in Google Scholar
  • 6c Hirt UH. Schuster MFH. French AN. Wiest OG. Wirth T. Eur. J. Org. Chem.  2001,  1569 
  • 7 Richardson RD. Wirth T. Angew. Chem. Int. Ed.  2006,  45:  4402 ; Angew. Chem. 2006, 118, 4510
    CrossrefPubMedSearch in Google Scholar
  • 8 Fuchigami T. Fujita T. J. Org. Chem.  1994,  59:  7190 
    CrossrefSearch in Google Scholar
  • 9a Ochiai M. Takeuchi Y. Katayama K. Sueda T. Miyamoto K. J. Am. Chem. Soc.  2005,  127:  12244 
    Search in Google Scholar
  • 9b Ochiai M. Miyamoto K. Eur. J. Org. Chem.  2008,  4229 
  • 10a Dohi T. Maruyama A. Yoshimura M. Morimoto K. Tohma H. Kita Y. Angew. Chem. Int. Ed.  2005,  44:  6193 ; Angew. Chem. 2005, 117, 6349
    Search in Google Scholar
  • 10b Dohi T. Kita Y. Chem. Commun.  2009,  2073 
  • 11 Richardson RD. Page TK. Altermann SM. Paradine SM. French AN. Wirth T. Synlett  2007,  538 
    Thieme Connect
  • 12 Dohi T. Maruyama A. Takenaga N. Senami K. Minamitsuji Y. Fujioka H. Caemmerer SB. Kita Y. Angew. Chem. Int. Ed.  2008,  47:  3787 ; Angew. Chem. 2008, 120, 3847
    CrossrefPubMedSearch in Google Scholar
  • 13a Reisinger CM. Wang X. List B. Angew. Chem. Int. Ed.  2008,  47:  8112 ; Angew. Chem. 2008, 120, 8232
    Search in Google Scholar
  • 13b Marigo M. Jørgensen KA. Chem. Commun.  2006,  2001 
  • 13c Momiyama N. Torii H. Saito S. Yamamoto H. Proc. Natl. Acad. Sci. U.S.A.  2004,  101:  5374 
    Search in Google Scholar
  • 13d Longbottom DA. Franckevicius V. Kumarn S. Oelke AJ. Wascholowski V. Ley SV. Aldrichimica Acta  2008,  41:  3 
    Search in Google Scholar
  • 14 Hassner A. Alexanian V. Tetrahedron Lett.  1978,  46:  4475 
    Search in Google Scholar
  • 15 Yamamoto Y. Togo H. Synlett  2006,  798 
    Thieme Connect
  • 16 Uyanik M. Yasui T. Ishihara K. Bioorg. Med. Chem. Lett.  2009,  19:  3848 
    CrossrefPubMedSearch in Google Scholar
  • 17 Boyd DR. Sharma ND. Smith AE. J. Chem. Soc., Perkin Trans. 1  1982,  2767 
    Crossref
  • 18 The absolute configuration was determined by independent synthesis of 3 from (S)-(-)-lactic acid: Imfeld M. Suchy M. Vogt P. Kucác P. Schlageter M. Widmer E. Helv. Chim. Acta  1982,  65:  1233 
    CrossrefSearch in Google Scholar