Ring Contraction of α,β-Unsaturated Cyclic Amines with cis-Dihydroxylation at the α,β-Position

Abstract

α,β-Unsaturated cyclic amines are oxidized by OsO4 to afford α,β-cis-dihydroxylated compounds which are thermodynamically transformed into ring-opened keto-alcohols. The keto-alcohols are then cyclized to form synthetically useful ring-contracted cyclic amines.