A General Synthetic Route to Enantiopure 5-Substituted cis-Decahydroquinolines

A practical synthetic route to enantiopure 5-substituted cis-decahydroquinolines has been developed, the key steps being a stereoselective cyclocondensation of 2-substituted 6-oxocyclohexenepropionates 2 with (R)-phenylglycinol, the stereoselective hydrogenation of the resulting unsaturated tricyclic lactams, and the stereoselective reductive cleavage of the oxazolidine ring.