Kinetic Resolution of Secondary Alcohols Using Chirality-Switchable Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-Dialkylaminopyrid-3-yl Pendants

摘要

We have established chiral macromolecular catalysts on the basis of single-handed helical poly(quinoxaline-2,3-diyl)s (PQX), whose screw-sense is switchable either to P- or M-helix by using different solvents. Introduction of achiral 4-(dialkylamino)pyrid-3-yl pendants onto the helically chiral PQX scaffold led us to find highly enantioselective nucleophilic catalyst in asymmetric Steglich rearrangement, in which enantioselection is switchable by changing reaction solvents.1 To explore new possibility of the helical polymer catalyst, we envisioned the use of the chirality-switchable helically chiral nucleophilic catalyst in kinetic resolution of secondary alcohols.