A copper-based catalytic technique for the regioselective hydroboration and hydrosilylation of dehydroalanine derivatives has been developed. This method introduces synthetically versatile boron and silicon groups, while simultaneously performing a catalytic anti-Markovnikov hydrofunctionalization of dehydroalanines and dehydropeptides for the synthesis of amino acids and peptides bearing unnatural side-chains. The products obtained were expediently converted into valuable nonproteinogenic amino acid building blocks for polypeptide synthesis.

Synthesis of Boron- and Silicon-Containing Amino Acids through Copper-Catalysed Conjugate Additions to Dehydroalanine Derivatives

BARTOCCINI, FRANCESCA;Silvia Bartolucci;LUCARINI, SIMONE;PIERSANTI, GIOVANNI
Membro del Collaboration Group
2015

Abstract

A copper-based catalytic technique for the regioselective hydroboration and hydrosilylation of dehydroalanine derivatives has been developed. This method introduces synthetically versatile boron and silicon groups, while simultaneously performing a catalytic anti-Markovnikov hydrofunctionalization of dehydroalanines and dehydropeptides for the synthesis of amino acids and peptides bearing unnatural side-chains. The products obtained were expediently converted into valuable nonproteinogenic amino acid building blocks for polypeptide synthesis.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11576/2626597
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