ol051242c_si_001.pdf (4.14 MB)
An Enantioselective Entry to cis-Perhydroisoquinolines
journal contribution
posted on 2005-08-18, 00:00 authored by Mercedes Amat, Maria Pérez, Annamaria T. Minaglia, Núria Casamitjana, Joan BoschAn enantioselective route to cis-perhydroisoquinolines, involving a cyclocondensation reaction of (R)-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 cis-octahydroisoquinolines bearing a quaternary
center at the C4-position.