Affiliation:
1. Department of Life Science and Applied Chemistry Graduate School of Engineering Nagoya Institute of Technology Gokiso, Showa-ku Nagoya 466-8555 Japan
2. The Institute of Scientific and Industrial Research Osaka University 8-1 Mihogaoka Ibaraki-shi Osaka 567-0047 Japan
Abstract
AbstractThe stereoselective reaction of α‐amido‐substituted malonic acid half oxyesters (α‐amido‐MAHOs) with isatins was developed. A cinchona alkaloid thiourea catalyst gave products bearing a tetrasubstituted stereogenic centre in high yields with high diastereo‐ and enantioselectivities (75–99% yield, 83:17–97:3 dr, 92:8–99:1 er). The obtained products can be converted into some chiral compounds without loss of enantiopurity. Density functional theory (DFT) calculations were conducted to clarify the origin of stereoselectivities, and suggested that the first stereogenic centre is set in the decarboxylation, the second in the protonation.
Funder
JFE 21st Century Foundation