One-Pot Synthesis of Chiral Piperidines Using Diphenylprolinol Silyl Ether

Abstract

A highly efficient four-component, one-pot synthesis of chiral piperidine derivatives with excellent diastereo- and enantioselectivities using a diphenylprolinol silyl ether catalyst is presented. Hayashi and co-workers obtained the desired products through a Michael reaction of an aldehyde and a nitroalkene, followed by aza-Henry reaction and Lewis acid catalyzed allylation or ­cyanation reaction. The authors also developed a synthesis of 2-allyloxy piperidine using an allyl ­alcohol instead of allylsilane or silyl cyanide as a nucleophile at the final step of this one-pot process.