An Enantioselective Entry to <i>cis</i>-Perhydroisoquinolines

An enantioselective route to <i>cis</i>-perhydroisoquinolines, involving a cyclocondensation reaction of (<i>R</i>)-phenylglycinol with a racemic oxoester, a stereoselective conjugate addition to an unsaturated bicyclic lactam, and the closure of the carbocyclic ring by a ring-closing metathesis as the key steps is reported. This route allows the preparation of 3-cyano derivatives as well as <i>cis</i>-octahydroisoquinolines bearing a quaternary center at the C4-position.