214072-03-4Relevant articles and documents
An access to (Z)-ethylenic pseudodipeptides based on ring-closing metathesis
Boucard, Valérie,Sauriat-Dorizon, Hélène,Guibé, Fran?ois
, p. 7275 - 7290 (2007/10/03)
A new access to enantiopure (Z)-ethylenic pseudopeptides, starting from the chiral pool of amino acids and enantiopure 2-substituted-but-3-enoic acids is proposed and illustrated by the syntheses of the (Z)-ethylenic pseudopeptidic analogs of L-Phe-L-Phe, L-Phe-D-Phe, L-Phe-L-Val, L-Phe-D-Val and racemic (LL,DD) and (LD,DL) (phenyl)Gly-Phe. The key-steps of these syntheses are a ring-closing metathesis, catalysed by Grubbs' ruthenium alkykidene complexes, on diethylenic amides and the hydrolytic cleavage of the resulting dihydropyridones under mild conditions through intermediate formation of cyclic imidates.
