Enantioselective and Rapid Rh-Catalyzed Arylation of <i>N</i>‑Tosyl- and <i>N</i>‑Nosylaldimines in Methanol

Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to <i>N</i>-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh­(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt₃ as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (<b>14</b>), an antagonist of the <i>N</i>-methyl-d-aspartate (NMDA) receptor

Enantioselective and Rapid Rh-Catalyzed Arylation of <i>N</i>‑Tosyl- and <i>N</i>‑Nosylaldimines in Methanol

Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to <i>N</i>-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh­(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt₃ as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (<b>14</b>), an antagonist of the <i>N</i>-methyl-d-aspartate (NMDA) receptor