Alkylation studies of a polyhydroxylated-cyano-piperidine scaffold

Abstract

Hexahydro -3-phenyl-6,7,8-trihydroxy-3R-[3α,5β,6β,7α,8β,8aβ]-5H-oxazolo[3,2-a]pyridine-5-carbonitrile is endowed with two non equivalent reactive sites: an α-amino nitrile at the C-5 position and an α-amino ether at the C-8a position. Herein, alkylation at the C-5 position was studied. The scope and limitations of these reactions have been investigated.