Synthesis 2012; 44(8): 1178-1182
DOI: 10.1055/s-0031-1290590
special topic
© Georg Thieme Verlag Stuttgart · New York

Chiral Aryl Iodide-Catalyzed Enantioselective α-Oxidation of Ketones

Arantxa Rodríguez
Department of Chemical & Biological Sciences, Queensgate, Huddersfield, HD1 3DH, UK, Fax: +44(1484)472182   Email: w.j.moran@hud.ac.uk
,
Wesley J. Moran*
Department of Chemical & Biological Sciences, Queensgate, Huddersfield, HD1 3DH, UK, Fax: +44(1484)472182   Email: w.j.moran@hud.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 09 February 2012

Accepted after revision: 24 February 2012

Publication Date:
16 March 2012 (online)

Abstract

Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective α-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.

 
  • References

    • For reviews, see:

    • 1a Merritt EA, Olofsson B. Synthesis 2011; 517
    • 1b Zhdankin VV. J. Org. Chem. 2011; 76: 1158
    • 1c Zhdankin VV. ARKIVOC 2009; 1
    • 1d Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
    • 1e Wirth T. Angew. Chem. Int. Ed. 2005; 44: 3656
    • 1f French AN, Bissmire S, Wirth T. Chem. Soc. Rev. 2004; 33: 354
    • 1g Zhdankin VV, Stang PJ. Chem. Rev. 2002; 102: 2523
    • 1h Koser GF. Aldrichimica Acta 2001; 34: 89
    • 1i Stang PJ, Zhdankin VV. Chem. Rev. 1996; 96: 1123
    • For selected examples, see:

    • 2a Rodríguez A, Moran WJ. Org. Lett. 2011; 13: 2220
    • 2b Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
    • 2c Dohi T, Kita Y. Chem. Commun. 2009; 2073
    • 2d Ochiai M, Miyamoto K. Eur. J. Org. Chem. 2008; 4229
    • 2e Richardson RD, Wirth T. Angew. Chem. Int. Ed. 2006; 45: 4402
  • 3 Koser GF, Relenyi AG, Kalos AN, Rebrovic L, Wettach RH. J. Org. Chem. 1982; 47: 2487
    • 4a Guilbault A.-A, Legault CY. ACS Catal. 2012; 2: 219
    • 4b Farooq U, Schäfer S, Shah A.-HA, Freudendahl DM, Wirth T. Synthesis 2010; 1023
    • 4c Altermann S, 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
    • 4d Richardson RD, Page TK, Altermann S, Paradine SM, French AN, Wirth T. Synlett 2007; 538
    • 4e Hirt UH, Spingler B, Wirth T. Eur. J. Org. Chem. 2001; 1569
    • 4f Hirt UH, Spingler B, Wirth T. J. Org. Chem. 1998; 63: 7674
    • 4g Wirth T, Hirt UH. Tetrahedron: Asymmetry 1997; 8: 23
    • 5a Uyanik M, Suzuki D, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2011; 50: 5331
    • 5b Uyanik M, Yasui T, Ishihara K. Bioorg. Med. Chem. Lett. 2009; 19: 3848
    • 5c Moriarty RM, Vaid RK, Hopkins TE, Vaid BK, Prakash O. Tetrahedron Lett. 1990; 31: 201
    • 6a Farid U, Wirth T. Angew. Chem. Int. Ed. 2012; 51 DOI: 10.1002/anie.201107703
    • 6b Röben C, Souto JA, González Y, Lishchynskyi A, Muñiz K. Angew. Chem. Int. Ed. 2011; 50: 9478
    • 6c Fujita M, Wakita M, Sugimura T. Chem. Commun. 2011; 47: 3983
    • 6d Fujita M, Yoshida Y, Miyata K, Wakisaka A, Sugimura T. Angew. Chem. Int. Ed. 2010; 49: 7068
    • 6e Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
    • 6f Uyanik M, Okamoto H, Yasui T, Ishihara K. Science 2010; 328: 1376
  • 7 Deur CJ, Miller MW, Hegedus LS. J. Org. Chem. 1996; 61: 2871
  • 8 Commercially available or readily prepared from 2-amino-3-methylbenzoic acid, see: Kanoh S, Muramoto H, Kobayashi M, Motoi M, Suda H. Bull. Chem. Soc. Jpn. 1987; 60: 3659