Synthesis of Chiral Azabicycles from Pyroglutaminols

Org Lett. 2016 Nov 4;18(21):5748-5751. doi: 10.1021/acs.orglett.6b03024. Epub 2016 Oct 27.

Abstract

The stereocontrolled synthesis of a range of substituted bicyclic morpholine and piperazine derivatives is reported from substituted pyroglutaminols via an intramolecular SN2 cyclization as the key step. This enantiospecific approach toward chiral bicyclic morpholines and piperazines offers new opportunities to access these challenging ring systems, which are becoming increasingly common motifs in drug discovery.

Publication types

  • Research Support, Non-U.S. Gov't