125844-06-6Relevant academic research and scientific papers
Boron analogues of valine, leucine, isoleucine, and phenylalanine: Syntheses of amine-alkyl(N-ethylcarbamoyl)boranes
Mills, Wyatt J.,Sutton, Christopher H.,Baize, Mark W.,Todd, Lee J.
, p. 1046 - 1052 (2008/10/08)
A series of recently prepared amine-alkylcyanoboranes (alkyl = i-Bu, sec-Bu, and benzyl; amine = pyridine and quinuclidine) have been treated with Et3OBF4 and then aqueous sodium hydroxide to form selected amine-alkyl(N-ethylcarbamoyl)boranes, which are some of the first reported analogues of the α-amino acids, leucine, isoleucine, and phenylalanine, respectively. Two intermediate nitrilium salts (sec-Bu and benzyl) have been fully characterized, demonstrating the unusual chemical stability of these boronium species. In addition, the full characterization of two amine-alkylcyanoboranes and one amine-alkyl(N-ethylcarbamoyl)borane (R = i-Pr; valine analogues) are reported.
Synthesis of Quinuclidine-Benzyl(ethylcarbamoyl)borane: The First Boron Analogue of a Phenylalanine Derivative
Mills, Wyatt J.,Todd, Lee J.,Huffman, John C.
, p. 900 - 902 (2007/10/02)
The title compound, the first non-glycine boron analogue of an α-amino acid derivative, was prepared by base hydrolysis of the N-ethylnitrilium salt of quinuclidine-benzylcyanoborane which is formed by treatment of the readily available quinuclidine-benzylborane with I2 and then sodium cyanide; the anaogue has been fully characterized spectroscopically and by X-ray diffraction.
