Stereoselective Synthesis of anti-1,3-Aminoalcohols via Reductive Opening of 4-Amidotetrahydropyrans Derived from the Prins/Ritter Sequence

A novel method has been devised for anti-1,3-aminoalcohols through reductive elimination of iodomethyltetrahydropyrans which are in turn derived from a Prins/Ritter reaction sequence. The synthetic versatility of this method has been explored in the total synthesis of piperidine alkaloids and β-amino acids.