Double Reductive Amination and Selective Strecker Reaction of a <scp>D</scp>‐Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5‐Trihydroxypiperidines

Abstract

Abstract A D ‐mannose‐derived aldehyde with the D ‐ lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5‐trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2‐cyanotrihydroxypiperidines through a highly regio‐ and diastereoselective Strecker reaction.