356796-87-7Relevant academic research and scientific papers
Expedient asymmetric synthesis of all four isomers of N,N′-protected 2,3-diaminobutanoic acid
Robinson,Stanislawski,Mulholland,He,Li
, p. 4148 - 4152 (2007/10/03)
2,3-Diaminobutanoic acid (DAB) is found in several peptide antibiotics, toxins, and biologically active molecules. This paper describes the practical and highly enantioselective synthesis of all four N,N′-protected DAB stereoisomers using an asymmetric Rh(I)-phosphine-catalyzed hydrogenation of isomeric enamides as the key step. Thermal and photochemical isomerization of the enamide hydrogenation substrates coupled with catalyst-geometric isomer pairing allows targeted synthesis of single DAB isomers in maximum yield.
