Synlett 2010(19): 2843-2846  
DOI: 10.1055/s-0030-1259013
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (E)-1-Benzyloxy-3-fluoro-1,3-butadiene: A Novel Fluorinated Diene for Diels-Alder Reactions

Tsuyoshi Hayashi, Yoshinosuke Usuki*, Yosuke Wakamatsu, Hideo Iio
Department of Material Science, Graduate School of Science, Osaka City University, Sugimoto, Sumioshi-ku, Osaka 558-8585, Japan
Fax: +81(6)66052522; e-Mail: [email protected];
Further Information

Publication History

Received 1 September 2010
Publication Date:
22 October 2010 (online)

Abstract

A new approach has been developed for the synthesis of the fluorinated Kitahara-Danishefsky’s diene analogue, (E)-1-benzyloxy-3-fluoro-1,3-butadiene, via a Pd-catalyzed process. This novel fluorine-containing diene reacts with various dienophiles to provide useful 1-fluorocyclohexene derivatives in good yields.

    References and Notes

  • 1a Fluorine in Medicinal Chemistry and Chemical Biology   Ojima I. Wiley-Blackwell; West Sussex: 2009. 
  • 1b Bégué JP. Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine   Wiley-VCH; Weinheim: 2008. 
  • For recent reviews, see:
  • 2a Kirk KL. J. Fluorine Chem.  2006,  127:  1013 
  • 2b Purser S. Moore PR. Swallow S. Gouverneur V. Chem. Soc. Rev.  2008,  37:  320 
  • 2c Hagmann WK. J. Med. Chem.  2008,  51:  4359 
  • 3 Diels O. Alder K. Ann.  1928,  460:  98 
  • 4 For a recent review on the pericyclic reactions of fluoroorganic compounds, see: Lam TH. Stanway SJ. Gouverneur V. Tetrahedron  2009,  65:  9905 
  • For recent examples of fluorinated dienophiles, see:
  • 5a Shastin AV. Nenajdenko VG. Muzalevskiy VM. Balenkova ES. Fröhlich R. Haufe G. Tetrahedron  2008,  64:  9725 
  • 5b Saito A. Yanai H. Sakamoto W. Takahashi K. Taguchi T. J. Fluorine Chem.  2005,  126:  709 
  • 6a Ibad MF. Abid O.-U.-R. Nawaz M. Adeel M. Villinger A. Langer P. Synlett  2010,  195 
  • 6b Paul K. Hwang JH. Choi JH. Jeong IH. Org. Lett.  2009,  11:  4728 
  • 6c Patrick TB. Gorrell K. Rogers J. J. Fluorine Chem.  2007,  128:  710 
  • 6d Pacheco M. Gouverneur V. Org. Lett.  2005,  7:  1267 
  • 6e Amii H. Kobayashi T. Terasawa H. Uneyama K. Org. Lett.  2001,  3:  3103 
  • 6f Kondo K. Cottens S. Schlosser M. Chem. Lett.  1984,  13:  2149 
  • 7a Danishefsky SJ. Kitahara T. J. Am. Chem. Soc.  1974,  96:  7807 
  • 7b Danishefsky SJ. Acc. Chem. Res.  1981,  14:  400 
  • 8a Kerwin JF. Danishefsky SJ. Tetrahedron Lett.  1982,  23:  3739 
  • 8b Josephsohn NS. Snapper ML. Hoveyda AH. J. Am. Chem. Soc.  2003,  125:  4018 
  • 9a Simonsen KB. Svenstrup N. Roberson M. Jorgensen KA. Chem. Eur. J.  2000,  6:  123 
  • 9b Motoyama Y. Koga Y. Nishiyama H. Tetrahedron  2001,  57:  853 
  • 10 Paredes E. Biolatto B. Kneeteman M. Mancini PM. Tetrahedron Lett.  2000,  41:  8079 
  • For diene formation resulting from β-elimination of the π-allyl complex, see:
  • 11a Bitar AY. Frontier AJ. Org. Lett.  2009,  11:  49 
  • 11b Takenaka H. Ukaji Y. Inomata K. Chem. Lett.  2005,  34:  256 
  • 11c Lee K.-Y. Kim Y.-H. Park M.-S. Ham W.-H. Tetrahedron Lett.  1998,  39:  8129 
  • 11d Keinan E. Kumar S. Dangar V. Vaya J. J. Am. Chem. Soc.  1994,  116:  11151 
  • 12 Danishefsky SJ. Yan C.-F. Singh RK. Gammill RB. McCurry PM. Fritsch N. Clardy J. J. Am. Chem. Soc.  1979,  101:  7001 
  • 13 Garbisch EW. J. Am. Chem. Soc.  1964,  86:  5561 
  • 14a Cossu S. Delogu G. De Lucchi O. Fabbri D. Licini G. Angew. Chem., Int. Ed. Engl.  1989,  28:  766 
  • 14b De Lucchi O. Fabbri D. Cossu S. J. Org. Chem.  1991,  56:  1888 
  • 15 Quirante J. Vila X. Bonjoch J. Synthesis  2001,  1971 
  • 16 Shi G.-Q. Cottens S. Shiba SA. Schlosser M. Tetrahedron  1992,  48:  10569 
  • 17 Achmatowicz O. Jurczak J. Konowal A. Zamojski A. Org. Magn. Res.  1970,  2:  55