Metal Triflate-Catalyzed One-Pot Synthesis of α-Aminophosphonates from Carbonyl Compounds in the Absence of Solvent

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

A simple and general method has been developed for one-pot three-component synthesis of α-aminophosphonates catalyzed by several metal triflates [M(OTf)_n, M = Li, Mg, Al, Cu, Ce] in the absence of solvent in good to high yields.

References

• 1 Sheridan RPJ. Chem. Inf. Comput. Sci.  2002,  42:  103 
  CrossrefGoogle Scholar
• 2a Grembecka J. Mucha A. Cierpicki T. Kafarski P. J. Med. Chem.  2003,  46:  2641 
  Google Scholar
• 2b Bird J. De Mello RC. Harper GP. Hunter DJ. Karran EH. Markwell RE. Miles-Williams AJ. Rahman SS. Ward RW. J. Med. Chem.  1994,  37:  158 
  Google Scholar
• 2c McLeod DA. Brinkworth RI. Ashly JA. Janda KD. Wirsching P. Bioorg. Med. Chem. Lett.  1991,  653 
  Google Scholar
• 2d Moore JD. Sprott KT. Fisher AJ. Tony M. Biochemistry  2002,  67:  8123 
  Google Scholar
• 2e Liu W. Rogers CJ. Fisher AJ. Toney M. Biochemistry  2002,  41:  12320 
  Google Scholar
• 2f Ranu BC. Hajra A. Jana U. Org. Lett.  1999,  1:  1141 
  Google Scholar
• 2g Kim KS. Hurh EY. Youn JN. Park JI. J. Org. Chem.  1999,  64:  9272 
  Google Scholar
• 2h Osipov SN. Artyushin OI. Kolomeits AF. Bruneau C. Dixneuf PH. Synlett  2000,  1031 
  Google Scholar
• 2i Kabachnik MI. Medved’ T. Ya. Dokl. Akad. Nauk SSSR  1952,  689 ; Chem. Abstr. 1953, 47, 1528
  Google Scholar
• 2j Fields EK. J. Am. Chem. Soc.  1952,  74:  1528 
  Google Scholar
• 2k Kuchar VP. Solodenko VA. Russ. Chem. Rev.  1987,  56:  1504 
  Google Scholar
• 2l Cherkasov RA. Galkin VI. Russ. Chem. Rev.  1998,  67:  940 
  Google Scholar
• 2m Kuchar VP. Svistunova NY. Solodenko VA. Soloshonok VA. Russ. Chem. Rev.  1993,  62:  284 
  Google Scholar
• 2n Uziel J. Genet JP. Zh. Org. Khim.  1997,  33:  1605 
  Google Scholar
• 3a Laschat S. Kunz H. Synthesis  1992,  90 
  CrossrefGoogle Scholar
• 3b Kudzin ZH. Lyzwa P. Luczak J. Andrijewski G. Synthesis  1997,  44 
  CrossrefGoogle Scholar
• 3c Yadav JS. Reddy BVS. Sarita Raj K. Bhaskar Reddy K. Prasad AR. Synthesis  2001,  2277 
  CrossrefGoogle Scholar
• 3d Lee S.-G. Park JH. Kang J. Lee JK. Chem. Commun.  2001,  1698 
  CrossrefGoogle Scholar
• 4 Saidi MR. Azizi N. Synlett  2002,  1347 
  Article in Thieme ConnectGoogle Scholar
• 5 Ranu BC. Hajra A. Jana U. Org. Lett.  1999,  1:  1141 
  CrossrefGoogle Scholar
• 6 Qian C. Huang T. J. Org. Chem.  1998,  63:  4125 
  CrossrefGoogle Scholar
• 7 Chandrasekhar S. Prakash SJ. Jagadeshwar V. Narsihmulu C. Tetrahedron Lett.  2001,  42:  5561 
  CrossrefGoogle Scholar
• 8 Yadav JS. Reddy BVS. Madan C. Synlett  2001,  1131 
  Article in Thieme ConnectGoogle Scholar
• 9 Kaboudin B. Nazari R. Tetrahedron Lett.  2001,  42:  8211 
  CrossrefGoogle Scholar
• 10 Akiyama T. Sanada M. Fuchibe K. Synlett  2003,  1463 
  Article in Thieme ConnectGoogle Scholar
• 11 Manabe K. Kobayashi S. Chem. Commun.  2000,  669 
  CrossrefGoogle Scholar
• 12 Ha H.-J. Nam G.-S. Synth. Commun.  1992,  22:  1143 
  CrossrefGoogle Scholar
• 13 Tanaka K. Toda F. Chem. Rev.  2000,  100:  1025 ; and references cited therein
  CrossrefGoogle Scholar
• 14a Firouzabadi H. Iranpoor N. Sobhani S. Tetrahedron Lett.  2002,  43:  3653 
  Google Scholar
• 14b Firouzabadi H. Iranpoor N. Sobhani S. Tetrahedron Lett.  2002,  43:  477 
  Google Scholar
• 14c Firouzabadi H. Iranpoor N. Sobhani S. Tetrahedron  2004,  45:  207 
  Google Scholar
• 14d Firouzabadi H. Iranpoor N. Sobhani S. Synthesis  2004,  290 
  Google Scholar
• 14e Firouzabadi H. Iranpoor N. Sobhani S. Amoozgar Z. Synthesis  2004,  295 
  Google Scholar
• 14f Firouzabadi H. Iranpoor N. Sobhani S. Amoozgar Z. Synthesis  2004,  in print 
  Google Scholar
• 15a Auge J. Leory F. Tetrahedron Lett.  1996,  37:  7715 
  Google Scholar
• 15b Corey EJ. Shimoji K. Tetrahedron Lett.  1983,  24:  169 
  Google Scholar
• 15c Yung Y. Diedench F. Selvestone G. J. Am. Chem. Soc.  1990,  112:  7829 
  Google Scholar
• 15d Jenkins CL. Kochi JK. J. Am. Chem. Soc.  1972,  94:  843 
  Google Scholar
• 15e Imamoto T. Koide Y. Hiyama S. Chem. Lett.  1990,  1445 
  Google Scholar