General synthesis of C-glycosyl amino acids via proline-catalyzed direct electrophilic alpha-amination of C-glycosylalkyl aldehydes.
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.
Nuzzi
Andrea
A
Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.
Massi
Alessandro
A
Dondoni
Alessandro
A
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004583:Electrons; D006031:Glycosylation; D015394:Molecular Structure
D000447:Aldehydes; D000596:Amino Acids