H. Sasai, S. Arai, Y. Tahara
Oct 1, 1995
Citations
0
Influential Citations
160
Citations
Quality indicators
Journal
Journal of Organic Chemistry
Abstract
{alpha}-Amino phosphonic acids 3 are interesting compounds in the design of enzyme inhibitors. The concept of mimicking tetrahedral transition states of enzyme-medicated peptide bond hydrolysis previously led to the successful design and synthesis of phosphonamide-containing peptides as a promising new class of proteinase inhibitors. It is not surprising that the absolute configuration of the {alpha}-carbon strongly influences the biological properties of 3. Several methods for the synthesis of optically active {alpha}-aminophosphonic acids have been published. The authors report here the first example of a catalytic asymmetric hydrophosphonylation to imines using lanthanoid-potassium-BINOL heterobimetallic complexes (LnPB, Ln = lanthanoid metal), which gives optically active {alpha}-amino phosphonates in modest to high enantiometric excess. 17 refs., 1 tab.