Synlett 2008(19): 3075-3076  
DOI: 10.1055/s-2008-1067280
© Georg Thieme Verlag Stuttgart ˙ New York


Fernanda Lacerda Silva da Machado*
Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, 21941-590 Rio de Janeiro, Brazil
Further Information

Publication History

Publication Date:
12 November 2008 (online)


Nitrosobenzene is a reagent used in many asymmetric syntheses with amazing results. It acts as an electrophile in catalytic enantioselective carbon-nitrogen and carbon-oxygen bond-forming reactions. It has received attention in recent years because of its high reactivity and regio- and stereoselectivities. In the presence of Lewis or ­Brønsted acid catalysts, enantioselective nitroso aldol or ­nitroso Diels-Alder reactions proceed under smooth conditions. [¹] Nitrosobenzene can be used in the aminoxylation of aldehydes and ketones, and the products are precursors of 1,2-amino alcohols, terminal diols [²] and allylic alcohols. [³] It can also be used in asymmetric desymmetrization of α-hydroxy ketones. [4] Others applications are described below. This reagent is stable, inexpensive and commercially available, all of which corroborate its use.


  • 1 Yamamoto H. Momiyama N. Chem. Commun.  2005,  3514 
  • 2 Brown SP. Brochu MP. Sinz CJ. MacMillan DWC. J. Am. Chem. Soc.  2003,  125:  10808 
  • 3 Zhong G. Yu Y. Org. Lett.  2004,  6:  1637 
  • 4 Ramachary DB. Barbas CF. Org. Lett.  2005,  7:  1577 
  • 5 Coleman G. H. McCloshey C. M. Stuart F. A. Bachaman W. E. Deno N. C. Edgerton R. F. Org. Synth. Coll. Vol. III  1955,  668 
  • 6 Srivastava RS. Tetrahedron Lett.  2003,  44:  3271 
  • 7 Momiyama N. Yamamoto H. Org. Lett.  2002,  4:  3579 
  • 8 Yamamoto Y. Momiyama N. Yamamoto H. J. Am. Chem. Soc.  2004,  126:  5962 
  • 9 Hayashi Y. Yamaguchi J. Sumiya T. Hibino K. Shoji M. J. Org. Chem.  2004,  69:  5966 
  • 10 Lemire A. Beaudoin MG. Charette AB. J. Org. Chem.  2005,  70:  2368