Synlett 2003(10): 1463-1464
DOI: 10.1055/s-2003-40858
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Brønsted Acid-Mediated Synthesis of α-Amino Phosphonates under Solvent-Free Conditions

Takahiko Akiyama*, Machiko Sanada, Kohei Fuchibe
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo 171-8588, Japan
Fax: +81(3)59921029; e-Mail: takahiko.akiyama@gakushuin.ac.jp;
Further Information

Publication History

Received 6 May 2003
Publication Date:
24 July 2003 (online)

Abstract

Three-component reactions of aldehydes, amine, and diethyl phosphite by means of CF3COOH under the solvent-free conditions afforded α-amino phosphonates in excellent yields.

    References

  • 1 Modern Solvents In Organic Synthesis, Topics In Current Chemistry   Vol. 206:  Knochel P. Houk KN. Kessler H. Springer Verlag; Berlin: 1999. 
  • 2 Curran DP. Pure Appl. Chem.  2000,  72:  1649 
  • 3 Leitner W. Top. Curr. Chem.  1999,  206:  107 
  • 4 Welton T. Chem. Rev.  1999,  99:  2071 
  • 5a Li C.-J. Chan T.-H. Organic Reactions in Aqueous Media   John Wiley; New York: 1997. 
  • 5b Organic Reactions in Water   Grieco P. Blackie Academic & Professional; London: 1998. 
  • 6a Toda F. Acc. Chem. Res.  1995,  28:  480 
  • 6b Metzger JO. Angew. Chem. Int. Ed.  1998,  37:  2975 
  • 6c Tanaka K. Toda F. Chem. Rev.  2000,  100:  1025 
  • For recent examples, see:
  • 7a Loh T.-P. Huang J.-M. Goh S.-H. Vittal JJ. J. Org. Chem.  2000,  2:  1291 
  • 7b Long J. Hu J. Shen X. Ji B. Ding K. J. Am. Chem. Soc.  2002,  124:  10 
  • 7c Kwong FY. Buchwald SL. Org. Lett.  2003,  5:  793 
  • 8a Hirschmann R. Smith AB. Taylor CM. Benkovic PA. Taylor SD. Yager KM. Sprengler PA. Venkovic SJ. Science  1994,  265:  234 
  • 9 Allen MC. Fuhrer W. Tuck B. Wade R. Wood JM. J. Med. Chem.  1989,  32:  1652 
  • 10a Laschat S. Kunz H. Synthesis  1992,  90 
  • 10b Yadav JS. Reddy BVS. Raj KS. Reddy KB. Prasad AR. Synthesis  2001,  2277 
  • 11a Heydari A. Javidan A. Shaffie M. Tetrahedron Lett.  2001,  42:  8071 
  • 11b Saidi MR. Azizi N. Synlett  2002,  1347 
  • 12 Ranu BC. Hajra A. Jana U. Org. Lett.  1999,  1:  1141 
  • 13a Qian C. Huang T. J. Org. Chem.  1998,  63:  4125 
  • 13b Manabe K. Kobayashi S. Chem. Commun.  2000,  669 
  • 13c Lee S. Park JH. Kang J. Lee JK. Chem. Commun.  2001,  1698 
  • 14 Chandrasekhar S. Prakash SJ. Jagadeshwar V. Narsihmulu C. Tetrahedron Lett.  2001,  42:  5561 
  • 15 Yadav JS. Reddy BVS. Madan C. Synlett  2001,  1131 
  • 16 Kaboudin B. Nazari R. Tetrahedron Lett.  2001,  42:  8211 
  • 17 Chandrasekhar S. Narsihmulu C. Sultana SS. Saritha B. Prakash SJ. Synlett  2003,  505 
  • 18 Klepacz A. Zwierzak A. Tetrahedron Lett.  2002,  43:  1079 
  • 19a Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1045 
  • 19b Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1426 
  • 19c Akiyama T. Takaya J. Kagoshima H. Tetrahedron Lett.  2001,  42:  4025 
  • 19d Akiyama T. Takaya J. Kagoshima H. Adv. Synth. Catal.  2002,  344:  338 
  • 19e Akiyama T. Itoh J. Fuchibe K. Synlett  2002,  1269 
  • 20 Akiyama T. Takaya J. Kagoshima H. Tetrahedron Lett.  1999,  40:  7831 
21

For the synthesis of α-amino phosphonate under solvent-free conditions, see; refs. [15-17]

22

Acetophenone did not react under the same reaction conditions.