ORGN 115 |
| A convenient method to access enantiomerically enriched tetrahydroisoquinoline 1-carboxylic acid (Tiq) derivatives was reported. Highly enantioselective addition of vinylzinc reagents to 3,4-dihydroisoquinoline N-oxide in the presence of N-acylethylenediamine ligands gave the chiral allylic hydroxyamines with up to 95% ee. The enantiomeric excess was further increased by recrystallization in hexanes and the ally adduct thus obtained was transformed to the unnatural Tiq amino acids in a two-step process. These types of isoquinoline structures with a chiral center at their C-1 position have appeared very useful in various biologically active natural alkaloids and as a scaffold in drug discovery. |
|
Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |