2-ACETHYLTHIAZOLE AS ATHREE-CARBON HOMOLOGATING REAGENT OF ALDEHYDES. APPLICATION TOWARD THE SYNTHESIS OF AMINO HEXOSES FROM L-SERINAL

Article abstract of DOI:10.1016/S0040-4039(01)93855-9

2-Acetylthiazole (1) serves as asource of the α-hydroxypropanal β-anion synthon for the conversion of aldehydes into syn and anti α,γ-dihydroxy homologues with three-more carbon atoms via a sequence consisting of:i) aldol condensation of the lithium enolate derived from 1; ii) reduction of the hydroxy ketone; iii) thiazole to formyl unmasking.The methodology is employed for the conversion of L-serinal into amino sugars.