Download PDF
Synthesis 2008(17): 2739-2742  
DOI: 10.1055/s-2008-1067210
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Coupling of Aldehydes, Homoallyl Alcohols, and Trimethylsilyl Azide: A Facile Synthesis of 4-Azidotetrahydropyrans via the Prins Cyclization

Jhillu S. Yadav*, Basi V. Subba Reddy, Tapas Maity, Gunda G. K. S. Narayana Kumar
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
Further Information

Publication History

Received 25 April 2008
Publication Date:
06 August 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

The coupling of aldehydes, homoallylic alcohols, and trimethylsilyl azide has been achieved in the presence of phosphomo­lybdic acid (PMA) in dichloromethane to produce 4-azido- ­tetrahydropyran derivatives in high yields with all cis selectivity. The use of a heteropoly acid makes this procedure simple, convenient, and cost effective.

Keywords

Prins cyclization - sodium azide - homoallylic alcohol - 4-azidotetrahydropyrans

    References

  • 1a Zhu J. Bienayme H. Multicomponent Reactions   Wiley; Weinheim: 2005. 
    Google Scholar
  • 1b Tietze LF. Beifuss U. Angew. Chem., Int. Ed. Engl.  1993,  32:  131 
    Google Scholar
  • 1c Tietze LF. Chem. Rev.  1996,  96:  115 
    Google Scholar
  • 2a Nicolaou KC. Sorensen EJ. Classics in Total Synthesis   VCH; Weinheim: 1996. 
    Google Scholar
  • 2b Perron F. Albizati KF. J. Org. Chem.  1987,  52:  4130 
    Google Scholar
  • 2c Class YJ. DeShong P. Chem. Rev.  1995,  95:  1843 
    Google Scholar
  • 2d Kopecky DJ. Rychnovsky SD. J. Am. Chem. Soc.  2001,  123:  8420 
    Google Scholar
  • 2e Wang Y. Janjic J. Kozmin SA. J. Am. Chem. Soc.  2002,  124:  13670 
    Google Scholar
  • 2f Aubele DL. Wan S. Floreancig PE. Angew. Chem. Int. Ed.  2005,  44:  3485 
    Google Scholar
  • 2g Bahnck KB. Rychnovsky SD. Chem. Commun.  2006,  2388 
    Google Scholar
  • 3a Snider BB. Hawryluk N. Org. Lett.  2000,  2:  635 
    Google Scholar
  • 3b Michelet V. Genet J.-P. Curr. Org. Chem.  2005,  9:  405 
    Google Scholar
  • 4a Suhara Y. Yamaguchi Y. Collins B. Schnaar RL. Yanagishita M. Hildreth JEK. Shimada I. Ichikawa Y. Bioorg. Med. Chem.  2002,  10:  1999 
    Google Scholar
  • 4b Hofle G. Steimnetz H. Gerth K. Reichenbach H. Liebigs Ann. Chem.  1991,  941 
    Google Scholar
  • 5a Prins HJ. Chem. Weekbl.  1919,  16:  1072 
    Google Scholar
  • 5b Adams DR. Bhatnagar SP. Synthesis  1977,  661 
    Google Scholar
  • 5c Yadav JS. Reddy BVS. Maity T. Kumar GGKSN. Tetrahedron Lett.  2007,  48:  7155 
    Google Scholar
  • 5d Yadav JS. Reddy BVS. Maity T. Kumar GGKSN. Tetrahedron Lett.  2007,  48:  8874 
    Google Scholar
  • 6a Wei ZY. Li JS. Wang D. Chan TH. Tetrahedron Lett.  1987,  28:  3441 
    Google Scholar
  • 6b Wei ZY. Wang D. Li JS. Chan TH. J. Org. Chem.  1989,  54:  5768 
    Google Scholar
  • 6c Coppi L. Ricci A. Taddei M. J. Org. Chem.  1988,  53:  913 
    Google Scholar
  • 6d Viswanathan GS. Yang J. Li CJ. Org. Lett.  1999,  1:  993 
    Google Scholar
  • 7a Kolb HC. Finn MG. Sharpless KB. Angew. Chem. Int. Ed.  2001,  40:  2004 
    Google Scholar
  • 7b Kolb HC. Sharpless KB. Drug Discovery Today  2003,  8:  1128 
    Google Scholar
  • 7c Breinbauer R. Kohn M. ChemBioChem  2003,  4:  1147 
    Google Scholar
  • 7d Bock VD. Hiemstra H. van Maarseveen JH. Eur J. Org. Chem.  2006,  51 
    Google Scholar
  • 8 Huisgen R. Angew. Chem., Int. Ed. Engl.  1963,  2:  565 
    CrossrefGoogle Scholar
  • 9a Tornøe CW. Christensen C. Meldal M. J. Org. Chem.  2002,  67:  3057 
    Google Scholar
  • 9b Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2596 
    Google Scholar
  • 10a Moorhouse AD. Santos AM. Gunaratnam M. Moore M. Neidle S. Moses JE. J. Am. Chem. Soc.  2006,  128:  15972 
    Google Scholar
  • 10b Lee LV. Mitchell ML. Huang S.-J. Fokin VV. Sharpless KB. Wong C.-H. J. Am. Chem. Soc.  2003,  125:  9588 
    Google Scholar
  • 11a Wu P. Feldman AK. Nugent AK. Hawker CJ. Scheel A. Voit B. Pyun J. Frechet JMJ. Harpless KB. Fokin VV. Angew. Chem. Int. Ed.  2004,  43:  3928 
    Google Scholar
  • 11b Wu P. Malkoch M. Hunt JN. Vestberg R. Kaltgrad E. Finn MG. Fokin VV. Sharpless KB. Hawker CJ. Chem. Commun.  2005,  5775 
    Google Scholar
  • 11c Rozkiewicz DI. Janczewski D. Verboom W. Ravoo BJ. Reinhoudt DN. Angew. Chem. Int. Ed.  2006,  45:  5292 
    Google Scholar
  • 12 Wang Q. Chan TR. Hilgraf R. Fokin VV. Sharpless KB. Finn MG. J. Am. Chem. Soc.  2003,  125:  3192 
    CrossrefPubMedGoogle Scholar
  • 13a Speers AE. Adam GC. Cravatt BF. J. Am. Chem. Soc.  2003,  125:  4686 
    Google Scholar
  • 13b Speers AE. Cravatt BF. Chem. Biol.  2004,  11:  535 
    Google Scholar
  • 13c Burley GA. Gierlich J. Mofid MR. Nir H. Tal S. Eichen Y. Carell T. J. Am. Chem. Soc.  2006,  128:  1398 
    Google Scholar
  • 14a Yadav JS. Subba Reddy BV. Narayana Kumar GGKS. Swamy T. Tetrahedron Lett.  2007,  48:  2205 
    Google Scholar
  • 14b Yadav JS. Subba Reddy BV. Narayana Kumar GGKS. Reddy MG. Tetrahedron Lett.  2007,  48:  4903 
    Google Scholar
  • 14c Yadav JS. Reddy MS. Prasad AR. Tetrahedron Lett.  2006,  47:  4995 
    Google Scholar
  • 15 Yadav JS. Subba Reddy BV. Mahesh Kumar G. Murty ChVSR. Tetrahedron Lett.  2001,  42:  89 
    CrossrefGoogle Scholar
  • 16a Alder RW. Harvey JN. Oakley MT. J. Am. Chem. Soc.  2002,  124:  4960 
    Google Scholar
  • 16b Ramesh J. Rychnovsky SD. Org. Lett.  2006,  8:  2175 
    Google Scholar
  • 16c Biermann U. Lützen A. Metzger JO. Eur. J. Org. Chem.  2006,  2631 
    Google Scholar