Enantioselective Synthesis of 4-Hydroxytetrahydropyridine Derivatives by Intramolecular Addition of Tertiary Enamides to Aldehydes

摘要

Chiral 4-hydroxypiperidine rings constitute the core structures of natural products such as dendrobate alkaloid 241D, lasubine I, and 13α-hydroxy-4-oxasparteine. Furthermore, a large number of 4-hydroxypiperidine derivatives have interesting bioactivity, ranging from activation of 5-hydroxytryptamine (5-HT_(1F)) receptors to inhibition of γ-secretase and the mammalian target of rapamycin. Despite their importance in varied disciplines, general synthetic methods for producing 4-hydroxypiperidine derivatives have remained scarcely explored.