Green Synthesis of α,β- and β,β-Dipeptides under Solvent-Free Conditions
作者:José G. Hernández、Eusebio Juaristi
DOI:10.1021/jo101159a
日期:2010.11.5
The reactivity of N-tert-butyloxycarbonyl-N-carboxyanhydrides derived from beta-alanine, (S)-beta(3-)homophenylglycine, and (S)-beta(3)-carboxyhomoglycine with different alpha- and beta-amino ester hydrochlorides was examined under ball-milling activation. In particular, good to excellent yields of several relevant alpha,beta- and beta,beta-dipeptides were obtained. An illustrative application of this methodology consisted in the high-yield synthesis of the mammalian alpha,beta-dipeptide N-Boc-L-carnosine-OMe.
Urethane <i>N</i>-Carboxyanhydrides from β-Amino Acids
A general method has been developed for the synthesis of N-tert-butyloxycarbonyl N-carboxyanhydridesfrom beta-amino acids using Vilsmeier complex. These beta-UNCA are stable, and the reactivity with different nucleophiles (alcohol, amine, lithium enolate) was studied.