A new approach to 2,2-disubstituted chromenes and tetrahydroquinolines through intramolecular cyclization of chiral 3,4-epoxy alcohols

An efficient route to chiral chromene and tetrahydroquinoline ring models 3 and 4 was developed by means of the vanadium epoxidation of chiral homoallylic alcohols 12 and 19 followed by an intramolecular epoxide opening of 3,4-epoxy alcohols 14 and 20. The configuration of all compounds was confirmed using NMR analysis.