Temperature-Controlled Diastereoselective Doebner/Ugi Tandem Reaction

Novel peptidomimetics containing a pyrrolone fragment were synthesized by a tandem combination of Doebner and Ugi type multicomponent reactions with controlled diastereoselectivity. This approach represents a convenient synthesis in the temperature range from 25 to 45 degrees C. In most cases, the new method allowed each diastereomer to be isolated separately.

Automated summary

This study describes the synthesis of novel peptidomimetics containing a pyrrolone fragment by a tandem combination of Doebner and Ugi type multicomponent reactions. The synthesis was performed at temperatures ranging from 25 to 45 degrees C and exhibited controlled diastereoselectivity. In most cases, each diastereomer could be isolated separately using this method.