ol0057939_si_002.pdf (144.89 kB)
Diastereoselective Protonation of Lactam Enolates Derived from (R)-Phenylglycinol. A Novel Asymmetric Route to 4-Phenyl-1,2,3,4-tetrahydroisoquinolines
journal contribution
posted on 2000-06-21, 00:00 authored by Nicolas Philippe, Vincent Levacher, Georges Dupas, Guy Quéguiner, Jean BourguignonHighly diastereoselective protonation of chiral lactam enolates of 4-substituted-1,4-dihydroisoquinolin-3-ones is reported. Protonation and
alkylation processes of these lactam enolates derived from phenylglycinol occur with opposite diastereofacial selectivity. This diastereoselective
protonation has been applied to the asymmetric synthesis of (4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 9 obtained in up to 97% ee.