ol0614525_si_001.pdf (1.72 MB)
Enantioselective Addition of Vinylzinc Reagents to 3,4-Dihydroisoquinoline N-Oxide
journal contribution
posted on 2006-08-31, 00:00 authored by Sa Wang, Christopher T. SetoLigand 2a promotes the enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide to yield chiral allylic hydroxylamines.
With 0.1 equiv of the ligand, the product is obtained in up to 84% ee, whereas with 1.2 equiv of the ligand, the ee is increased to the 90−95%
range with a variety of aliphatic, cyclic, and aromatic vinylzinc reagents. This method was used to synthesize the protected unnatural amino
acid N-Cbz-d-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid in three steps from the allylic hydroxylamine.