Rapid Assembly of Molecular Complexity from Simple Enamides

Abstract

The efficient assembly of structurally complex molecules containing multiple continuous stereogenic centers still constitutes a tremendous challenge for any synthetic organic chemist. In this article, we briefly summarize our recent advances in the utilization of enamides as versatile building blocks for the rapid and highly stereoselective construction of different molecular scaffolds containing up to five continuous stereocenters.

I2 or I2/PIFA one-pot induced system for rapid synthesis of chalcogenated enamides, uracils or 2-pyridones under mild conditions

“…Enamides, 1 along with structurally related compounds such as 2-pyridones 2 and uracils, 3 hold allure in contemporary organic synthetic chemistry. They are prevalent in various living organisms and plants, and can be easily transformed into a diverse array of biologically significant natural products or pharmaceutically active molecules.…”

Brønsted Acid-Catalyzed Diastereoselective Synthesis of Spiroisoindolinones from Enamides

“…In all of these reports, the formation of an electrophilic acylimine species 2 as the first key intermediate is proposed. Our group has successfully exploited the addition of enamides to similar acylimine species as the key step in the development of novel highly stereoselective transformations . Recently, we were able to extend our methods to the stereoselective synthesis of different heterocyclic scaffolds .…”