Enantioselective Control of Both Helical and Axial Stereogenic Elements though an Organocatalytic Approach

Abstract

A highly diastereo- and enantio-selective method for the asymmetric synthesis of molecules containing helicenes and stereogenic axes was developed based on organocatalysis. Various compounds bearing both helical and axial stereogenic elements were obtained in excellent enantioselectivities. The mechanism study revealed that the reaction proceeded through two stages: 1) The first cyclization produces a reaction intermediate containing a stereogenic axis. 2) The dynamic kinetic resolution of helix reaction intermediate following with cyclization generates a helix and another stereogenic axis.

Keywords: asymmetric catalysis; axial chirality; helicene; organocatalysis.