期刊
AMINO ACIDS
卷 51, 期 10-12, 页码 1475-1483出版社
SPRINGER WIEN
DOI: 10.1007/s00726-019-02782-7
关键词
alpha; beta dipeptides; Allylic amination; Steric hindrance; Alkylidene acetacetamides; Cyclic scaffolds
The synthesis of alpha/beta dipeptides containing linear or cyclic alpha-dehydro-beta-amino acids has been performed starting from alkylidene acetacetamides, which were obtained from alpha-amino esters via Ir-catalyzed allylic amination. Differently hindered carbonates were synthesized via a protocol involving chemoselective Luche's reduction, acylation, and allylic amination. Depending on the nature of the selected alpha-amino acid, we observed strong influence on the product regiochemistry due to the carbonate size and the amino-acid side chain. In particular, complete regioselectivity was observed in the aminic allylation of carbonates deriving from amino acids possessing a methylene unit in beta-position. On the contrary, methyl carbonates deriving from beta-branched amino acid afforded different results depending on the hindrance of the carbonate. Moreover, spontaneous cyclization was observed for carbamate-containing intermediates, allowing to obtain peptidomimetic polyfunctionalized dihydropyrimidine-2,4-dione. Finally, by inverting the order of reduction/acylation steps on the starting alkylidene acetoacetamides, the formation of polyfunctionalized 1,3-oxazinane-2,4-dione was obtained demonstrating the wide applications of these substrates for the preparation of bioactive peptidomimetics.
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