General Synthesis of <i>C</i>-Glycosyl Amino Acids via Proline-Catalyzed Direct Electrophilic α-Amination of <i>C</i>-Glycosylalkyl Aldehydes

Abstract

Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de >95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.