Tritylamine (Triphenylmethylamine) in Organic Synthesis; I. The Synthesis ofN-(Triphenylmethyl)alkanimines, 1-(Triphenylmethylamino)alkylphosphonic Esters, and 1-Aminoalkylphosphonic Acids and Esters
Application of in Situ Silylation for Improved, Convenient Preparation of Fluorenylmethoxycarbonyl (Fmoc)-Protected Phosphinate Amino Acids
作者:Li、John K. Whitehead、Robert P. Hammer
DOI:10.1021/jo070266p
日期:2007.4.1
A convenient and efficient method has been developed for the preparation of 9-fluorenylmethoxycarbonyl (Fmoc)-protected 1-aminoalkylphosphinic acids. Reproducible procedures for the synthesis and purification of free α-amino H-phosphinates are provided. Protection of free aminophosphinates as the N-Fmoc derivative was achieved by in situ trimethylsilylation of aminoalkylphosphinic acids, which then
A facile method for the preparation of both 2-pyrrolidinyl-substituted phosphinic acids and 1-aminoalkylphosphinic acids is described. Reaction of 1-pyrroline trimer or N-tritylalkanamine with bis(trimethylsilyl)phosphonite, followed by silylation with N,O-bis(trimethylsilyl)acetamide gives an intermediate which is used in a Michael addition reaction or an Arbuzov reaction.