Synthesis 2008(18): 3009-3011  
DOI: 10.1055/s-2008-1067251
© Georg Thieme Verlag Stuttgart ˙ New York

DBU-Catalyzed Addition Reactions of Sulfonylimidates

Ryosuke Matsubara, Shu Kobayashi*
Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Fax: +81(3)56840634; e-Mail: [email protected];
Further Information

Publication History

Received 14 July 2008
Publication Date:
04 September 2008 (online)


Sulfonylimidates react with various types of N-protected imines in the presence of a catalytic amount of DBU to afford β-aminosulfonylimidates in high yields and high anti-selectivities. The experimental procedure is described in detail.


  • 1a Harada S. Handa S. Matsunaga S. Shibasaki M. Angew. Chem. Int. Ed.  2005,  44:  4439 
  • 1b Morimoto H. Wiedeman SH. Yamaguchi A. Harada S. Chien Z. Matsunaga S. Shibasaki M. Angew. Chem. Int. Ed.  2006,  45:  3146 
  • 1c Marigo M. Kjarsgaard K. Juhl K. Gathergood N. Jørgensen KA. Chem. Eur. J.  2003,  9:  2359 
  • 1d Hamashima Y. Sasamoto N. Hotta D. Somei H. Umebayashi N. Sodeoka M. Angew. Chem. Int. Ed.  2005,  44:  1549 
  • 1e Bernardi L. Gothelf AS. Hazell RG. Jørgensen KA. J. Org. Chem.  2003,  68:  2583 
  • 1f Ooi T. Kameda M. Fujii JI. Maruoka K. Org. Lett.  2004,  6:  2397 
  • 1g Kobayashi J. Yamashita Y. Kobayashi S. Chem. Lett.  2005,  34:  268 
  • 1h Salter MM. Kobayashi J. Shimizu Y. Kobayashi S. Org. Lett.  2006,  8:  3533 
  • 2 Matsubara R. Berthiol F. Kobayashi S. J. Am. Chem. Soc.  2008,  130:  1804 
  • 3a Kupfer R. Nagel M. Würthwein E.-U. Allmann R. Chem. Ber.  1985,  118:  3089 
  • 3b Walter W. Krohn J. Liebigs Ann. Chem.  1973,  443 
  • 3c Yoo EJ. Bae I. Cho SH. Han H. Chang S. Org. Lett.  2006,  8:  1347 ; and references cited therein
  • 5a Kanazawa AM. Denis J.-N. Greene AE. J. Am. Chem. Soc.  1994,  59:  1238 
  • 5b Vishwakarma LC. Stringer OD. Davis FA. Org. Synth.  1987,  66:  203 
  • 5c Love BE. Raje PS. Williams TC. Synlett  1994,  493 
  • 5d Hodous BL. Fu GC. J. Am. Chem. Soc.  2002,  124:  1578 
  • 5e Hagiwara E. Fujii A. Sodeoka M. J. Am. Chem. Soc.  1998,  120:  2474 

Thorough evaporation of the solvents provided the imidate HCl salt (a solid). The solidification of imidate salt could be encouraged by keeping it under argon at -20 ˚C. The exposure to air should be avoided as this salt readily absorbs moisture to form a gum-like solid, from which it was found to be difficult to remove the starting materials.