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

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.

phosphonates - imines - nucleophilic additions - amine - diethyl phosphite

References

<A NAME="RU08503ST-1">1</A> Modern Solvents In Organic Synthesis, Topics In Current Chemistry   Vol. 206:  Knochel P. Houk KN. Kessler H. Springer Verlag; Berlin: 1999. 

<A NAME="RU08503ST-2">2</A> Curran DP. Pure Appl. Chem.  2000,  72:  1649 

<A NAME="RU08503ST-3">3</A> Leitner W. Top. Curr. Chem.  1999,  206:  107 

<A NAME="RU08503ST-4">4</A> Welton T. Chem. Rev.  1999,  99:  2071 

<A NAME="RU08503ST-5A">5a</A> Li C.-J. Chan T.-H. Organic Reactions in Aqueous Media   John Wiley; New York: 1997. 

<A NAME="RU08503ST-5B">5b</A> Organic Reactions in Water   Grieco P. Blackie Academic & Professional; London: 1998. 

<A NAME="RU08503ST-6A">6a</A> Toda F. Acc. Chem. Res.  1995,  28:  480 

<A NAME="RU08503ST-6B">6b</A> Metzger JO. Angew. Chem. Int. Ed.  1998,  37:  2975 

<A NAME="RU08503ST-6C">6c</A> Tanaka K. Toda F. Chem. Rev.  2000,  100:  1025 

For recent examples, see:

<A NAME="RU08503ST-7A">7a</A> Loh T.-P. Huang J.-M. Goh S.-H. Vittal JJ. J. Org. Chem.  2000,  2:  1291 

<A NAME="RU08503ST-7B">7b</A> Long J. Hu J. Shen X. Ji B. Ding K. J. Am. Chem. Soc.  2002,  124:  10 

<A NAME="RU08503ST-7C">7c</A> Kwong FY. Buchwald SL. Org. Lett.  2003,  5:  793 

<A NAME="RU08503ST-8A">8a</A> Hirschmann R. Smith AB. Taylor CM. Benkovic PA. Taylor SD. Yager KM. Sprengler PA. Venkovic SJ. Science  1994,  265:  234 

<A NAME="RU08503ST-9">9</A> Allen MC. Fuhrer W. Tuck B. Wade R. Wood JM. J. Med. Chem.  1989,  32:  1652 

<A NAME="RU08503ST-10A">10a</A> Laschat S. Kunz H. Synthesis  1992,  90 

<A NAME="RU08503ST-10B">10b</A> Yadav JS. Reddy BVS. Raj KS. Reddy KB. Prasad AR. Synthesis  2001,  2277 

<A NAME="RU08503ST-11A">11a</A> Heydari A. Javidan A. Shaffie M. Tetrahedron Lett.  2001,  42:  8071 

<A NAME="RU08503ST-11B">11b</A> Saidi MR. Azizi N. Synlett  2002,  1347 

<A NAME="RU08503ST-12">12</A> Ranu BC. Hajra A. Jana U. Org. Lett.  1999,  1:  1141 

<A NAME="RU08503ST-13A">13a</A> Qian C. Huang T. J. Org. Chem.  1998,  63:  4125 

<A NAME="RU08503ST-13B">13b</A> Manabe K. Kobayashi S. Chem. Commun.  2000,  669 

<A NAME="RU08503ST-13C">13c</A> Lee S. Park JH. Kang J. Lee JK. Chem. Commun.  2001,  1698 

<A NAME="RU08503ST-14">14</A> Chandrasekhar S. Prakash SJ. Jagadeshwar V. Narsihmulu C. Tetrahedron Lett.  2001,  42:  5561 

<A NAME="RU08503ST-15">15</A> Yadav JS. Reddy BVS. Madan C. Synlett  2001,  1131 

<A NAME="RU08503ST-16">16</A> Kaboudin B. Nazari R. Tetrahedron Lett.  2001,  42:  8211 

<A NAME="RU08503ST-17">17</A> Chandrasekhar S. Narsihmulu C. Sultana SS. Saritha B. Prakash SJ. Synlett  2003,  505 

<A NAME="RU08503ST-18">18</A> Klepacz A. Zwierzak A. Tetrahedron Lett.  2002,  43:  1079 

<A NAME="RU08503ST-19A">19a</A> Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1045 

<A NAME="RU08503ST-19B">19b</A> Akiyama T. Takaya J. Kagoshima H. Synlett  1999,  1426 

<A NAME="RU08503ST-19C">19c</A> Akiyama T. Takaya J. Kagoshima H. Tetrahedron Lett.  2001,  42:  4025 

<A NAME="RU08503ST-19D">19d</A> Akiyama T. Takaya J. Kagoshima H. Adv. Synth. Catal.  2002,  344:  338 

<A NAME="RU08503ST-19E">19e</A> Akiyama T. Itoh J. Fuchibe K. Synlett  2002,  1269 

<A NAME="RU08503ST-20">20</A> Akiyama T. Takaya J. Kagoshima H. Tetrahedron Lett.  1999,  40:  7831 

<A NAME="RU08503ST-21">21</A>

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

<A NAME="RU08503ST-22">22</A>

Acetophenone did not react under the same reaction conditions.