Synlett 2009(17): 2880-2881  
DOI: 10.1055/s-0029-1218101
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Bestmann-Ohira Reagent: A Versatile Reagent in Organic Synthesis

Umesh Daga Patil
Department of Organic Chemistry, North Maharashtra University, Umavinagar, Jalgaon 425001, India
e-Mail: umesh123patil@gmail.com;
Further Information

Publication History

Publication Date:
02 October 2009 (online)

Introduction

Bestmann-Ohira reagent [(1-diazo-2-oxopropyl)phosphonate] can be prepared by the reaction of dimethyl-2-oxopropylphosphonate, TosN3 [¹a] or p-acetamidobenzenesulfonyl azide, [¹b] NaH, t-BuOK or Et3N in benzene and THF. An alternative is the preparation using polymer-supported sulfonyl azide and t-BuOK in methylenchloride. [¹c] The Bestmann-Ohiro reagent is widely used in the conversion of primary alcohols, aldehydes, ketones, and amides into alkynes. Recently, it was employed in the synthesis of pyrazoles as well as 1,3-oxazoles.

Scheme 1

    References

  • 1a Callant P. D’haenens L. Vandewalle M. Synth. Commun.  1984,  14:  155 
  • 1b Pietruszka J. Witt A. Synthesis  2006,  4266 
  • 1c Harned AM. Sherrill WM. Flynn DL. Hanson PR. Tetrahedron  2005,  61:  12093 
  • 2 Müller S. Liepold B. Bestmann HJ. Synlett  1996,  521 
  • 3 Dickson HD. Smith SC. Hinkle KW. Tetrahedron Lett.  2004,  45:  5597 
  • 4 Quesada E. Taylor RJK. Tetrahedron Lett.  2005,  46:  6473 
  • 5 Muruganantham R. Mobin SM. Namboothiri INN. Org. Lett.  2007,  9:  1125 
  • 6 Gong D. Zhang L. Yuan C. Synth. Commun.  2004,  34:  3259 
  • 7 Clay MD. Fallis AG. Angew. Chem. Int. Ed.  2005,  44:  4039 
  • 8 Barrett AGM. Hopkins BT. Love AC. Tedeschi L. Org. Lett.  2004,  6:  835 
  • 9 Bartnik R. Lesniak S. Wasiak P. Tetrahedron Lett.  2004,  45:  7301 
  • 10 Gilbert JC. Weerasooriya U. J. Org. Chem.  1982,  47:  1837 
  • 11 Ohira S. Synth. Commun.  1989,  19:  561