Download PDF
Synthesis 2011(10): 1537-1540  
DOI: 10.1055/s-0030-1260007
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Et2MeN×HI-Catalyzed Reaction of Arylboronic Acids with 2-Acyl-2,3-dihydro-4H-pyrans Leading to 2-Aryltetrahydrocyclopenta[1,3,2]dioxaboroles

Takahide Fukuyama*, Takahiro Okamura, Ilhyong Ryu
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
Fax: +81(72)2549695; e-Mail: fukuyama@c.s.osakafu-u.ac.jp;
Further Information

Publication History

Received 8 October 2010
Publication Date:
15 April 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

The reaction of arylboronic acids with 2-acyl-2,3-dihydro-4H-pyrans proceeded smoothly in the presence of a catalytic amount of Et2MeN˙HI to give acyl-substituted 2-aryltetrahydrocyclopenta[1,3,2]dioxaboroles in good yields. The reaction is likely to involve the acid-catalyzed ring-opening reaction of pyrans, an intramolecular aldol reaction, and condensation with boronic acids.

Key words

ring contraction - dihydropyran - boronic acid - cyclopentanediol - boronic ester

    References

  • For reviews on ring-contraction reactions, see:
  • 1a Redmore D. Gutsche CD. Carbocyclic Ring Contraction Reactions, In Advances in Alicyclic Chemistry   Vol. 3:  Hart H. Karabastos GJ. Academic Press; New York: 1971.  p.1-138  
    Google Scholar
  • 1b Silva LF. Tetrahedron  2002,  58:  9132 
    Google Scholar
  • 2 For a review on Wolff rearrangement, see: Gill GB. The Wolff Rearrangement, In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.887-912  
    Google Scholar
  • 3 For a review on Favorskii rearrangement, see: Mann J. The Favorskii Rearrangement, In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.839-859  
    Google Scholar
  • 4 For a review on Wagner-Meerwein rearrangement, see: Hanson JR. The Wagner-Meerwein Rearrangement, In Comprehensive Organic Synthesis   Vol. 3:  Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.705-719  
    Google Scholar
  • For recent examples on total synthesis of natural product using ring contraction, see:
  • 5a Jana CK. Scopelliti R. Gademann K. Chem. Eur. J.  2010,  16:  7692 
    Google Scholar
  • 5b Fu L. Gribble GW. Tetrahedron Lett.  2010,  51:  537 
    Google Scholar
  • 5c Carnerio VMT. Ferraz HMC. Vieira TO. Ishikawa EE. Silva LF. J. Org. Chem.  2010,  75:  2877 
    Google Scholar
  • 5d Lee H.-Y. Murugan RN. Moon DK. Eur. J. Org. Chem.  2009,  5028 
    Google Scholar
  • 5e Silva LF. Craveiro MV. Org. Lett.  2008,  10:  5417 
    Google Scholar
  • 5f Pouysegu L. Marguerit M. Gagnepain J. Lyvinec G. Eatherton AJ. Quideau S. Org. Lett.  2008,  10:  5211 
    Google Scholar
  • 5g Angeles AR. Waters SP. Danishefsky SJ. J. Am. Chem. Soc.  2008,  130:  13765 
    Google Scholar
  • 6a Fukuyama T. Yamaura R. Higashibeppu Y. Okamura H. Ryu I. Kondo T. Mitsudo T. Org. Lett.  2005,  7:  5781 
    Google Scholar
  • 6b Fukuyama T. Higashibeppu Y. Yamaura R. Ryu I. Org. Lett.  2007,  9:  587 
    Google Scholar
  • 6c Fukuyama T. Doi T. Minamino S. Omura S. Ryu I. Angew. Chem. Int. Ed.  2007,  46:  5559 
    Google Scholar
  • 7 Chaquin P. Morizur J.-P. Kossanyi J. J. Am. Chem. Soc.  1977,  99:  903 
    CrossrefGoogle Scholar