New non-proteogenic aminoacids bearing an enol aryl-ether moiety

Article abstract of DOI:10.1016/S0040-4020(01)88758-5

Aminoacids bearing an enol aryl-ether moiety have been synthesized by a new method allowing a great versatility in the introduction of N-protective groups and enol ether functions. This method involves a Wittig-Horner condensation affording alpha, beta-dehydrohomoserine ether derivatives, followed by a regio and stereoselective isomerization into the desired E enol ether. Clean deprotection was achieved providing new 2-amino-4-aryloxybut-3(E)-enoic acids 3.