C-silylation of secondary amides: GlcNAc peracetate derivatives

Article abstract of DOI:10.1016/0040-4039(95)01559-0

The Me₃SiOTf-promoted formation of GlcNAc 1,2-cis oxazoline from GlcNAc peracetates can give significant amounts of nonpolar by-products. We identified these by-products to be C-silylated esters and amides. Secondary amides are readily C-silylated by treatment with a mixture of Me₃SIOTf and NEt₃. These C-silylated secondary amides are useful, as they undergo fluoride ion promoted aldol condensation.