ORGN 11 |
First catalytic asymmetric aza-Henry reaction of nitro compounds with imines: A novel approach to optically active a,b-diamino acid derivatives
| Kristian Rahbek Knudsen, Nagatoshi Nishiwaki, Tine Risgaard, Kurt V. Gothelf, and Karl Anker Jørgensen. Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000 Arhus C, Denmark |
The Henry (nitro aldol) reaction and its aza analogue are fundamental C-C bond forming reactions in organic chemistry. Compared with the development of catalytic enantioselective aldol reactions, there are only few examples of catalytic asymmetric nitro aldol reactions. We present the first catalytic highly diastereo- and enantioselective aza-Henry reaction, employing either nitro compounds, in combination with a base, or silyl nitronates. The reaction proceeds in high yields with enantioselectivities up to 99% and with remarkable diastereoselectivities up to 39:1. The obtained product can be reduced to afford optically active a,b-diamino acid derivatives. |
| |
|
|