A concise synthesis of homochiral sedamines and related alkaloids. A new reductive application of Jacobsen's catalyst

Article abstract of DOI:10.1016/S0040-4039(99)01341-6

Two methods for the generation of both enantiomers of sedamine [1- methyl-2-(2-phenyl-2-hydroxy-1-ethyl)piperidine] in high optical purity have been elaborated. The first utilises the lipase-mediated kinetic resolution of racemic acetates and the second involves the NaBH₄ mediated reduction of ketones catalysed by Jacobsen's catalyst. Some related applications of these reactions are also disclosed.