An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27–72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids.

Graphical abstractFour exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27%–72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids.Figure optionsDownload full-size imageDownload as PowerPoint slide