TiCl4-Catalyzed Efficient One-Pot Synthesis of α α-Amino Phosphonates

α-Aminophosphonates are synthesized by three-component condensation of aldehydes, amines, and trimethylphosphite in acetonitrile by using TiCl4 as catalyst. Compared to conventional methods, this new method consistently has advantages, including excellent yields, short reaction times, and mild reaction conditions.

[1]  N. Azizi,et al.  A New Protocol for a One-pot Synthesis of α-Amino Phosphonates by Reaction of Imines Prepared In Situ with Trialkylphosphites , 2002 .

[2]  R. Nazari,et al.  Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions , 2001 .

[3]  B. Kaboudin Surface-Mediated Solid Phase Reactions: A Simple and New Method for the Synthesis of α-Aminophosphonates under Solvent-Free Conditions , 2001 .

[4]  A. Heydari,et al.  One-pot synthesis of N-trimethylsilyloxy-α-amino phosphonates from aldehydes using lithium perchlorate/diethyl ether as a catalyst , 2001 .

[5]  J. Yadav,et al.  Zr4+-Catalyzed Efficient Synthesis of α-Aminophosphonates , 2001 .

[6]  J. Yadav,et al.  Montmorillonite Clay-Catalyzed One-Pot Synthesis of α-Amino Phosphonates , 2001 .

[7]  B. Ranu,et al.  General Procedure for the Synthesis of α-Amino Phosphonates from Aldehydes and Ketones Using Indium(III) Chloride as a Catalyst , 1999 .

[8]  钱长涛,et al.  One-pot synthesis of α-amino phosphonates from aldehydes using lanthanide triflate as a catalyst , 1998 .

[9]  S. Shibuya,et al.  Stereoselective Synthesis of .beta.-Oxygenated .alpha.-Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of .alpha.-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogs of Oxyamino Acids , 1994 .

[10]  S. Benkovic,et al.  Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids. , 1994, Science.

[11]  C. Yuan,et al.  Studies on Organophosphorus Compounds; LXIII. A New and Facile Synthetic Route to Protected Phosphonodipeptides: A Backbone for the Formation of Oligophosphonopeptides , 1992 .

[12]  Paweł Kafarski,et al.  BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDS , 1991 .

[13]  P. Wieczorek,et al.  Plant‐growth‐regulating phosphono peptides , 1990 .

[14]  J. Wood,et al.  Renin inhibitors. Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond. , 1989, Journal of medicinal chemistry.

[15]  I. A. Natchev Synthesis, enzyme — substrate interaction, and herbicidal activity of phosphoryl analogues of glycine , 1988 .

[16]  V. Kukhar,et al.  The Phosphorus Analogues of Aminocarboxylic Acids , 1987 .

[17]  P. Bartlett,et al.  Phosphorus amino acid analogues as inhibitors of leucine aminopeptidase. , 1987, Journal of medicinal chemistry.

[18]  C. Hassall,et al.  Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. , 1986, Journal of medicinal chemistry.

[19]  C. D. Campbell,et al.  1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids , 1985 .

[20]  K. More,et al.  Alkylation and silicon Pummerer rearrangement of chloromethyl phenyl sulfoxide. A thiol ester acyl anion equivalent , 1978 .

[21]  Ellis K. Fields,et al.  The Synthesis of Esters of Substituted Amino Phosphonic Acids1a , 1952 .