Synthesis of Glycosyl Amides Using Selenocarboxylates as Traceless Reagents for Amide Bond Formation.
Carbohydrate-derived amides were successfully prepared in good yields from a broad range of substrates, including furanosyl and pyranosyl derivatives. The methodology successfully relied on the in situ generation of lithium selenocarboxylates from Se/LiEt3BH and acyl chlorides or carboxylic acids and their reaction with sugar azides. A key aspect of the present protocol is that we start from elemental selenium; isolation and handling of all reactive and sensitive selenium-containing intermediates is avoided, therefore providing the selenocarboxylate the status of a traceless reagent.
Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS , Av. Bento Gonçalves 9500, 91501-970, Porto Alegre, RS, Brazil.
Luana
L
Silva
Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS , Av. Bento Gonçalves 9500, 91501-970, Porto Alegre, RS, Brazil.
Ricardo F
RF
Affeldt
Instituto de Química, Universidade Federal do Rio Grande do Sul, UFRGS , Av. Bento Gonçalves 9500, 91501-970, Porto Alegre, RS, Brazil.
Diogo S
DS
Lüdtke