Diastereoselective intramolecular O-allylation with alkynes using palladium/Brønsted acid combined catalysis: access to substituted chiral oxazolidines

Abstract

A Pd-catalyzed highly diastereoselective intramolecular allylation of O-nucleophiles with N-tethered alkynes has been developed. The reaction utilizes Brønsted acid as a co-catalyst and provides a completely atom-economic pathway to access functionalized chiral oxazolidines. Moreover, the enantiomerically pure substrates have been derived from simple, inexpensive chiral amino alcohols.