Chemodivergent reactions have emerged as important synthetic tools in organic synthesis providing easy and selective access to divergent products. The switch in selectivity can be performed by simply switching the metal-catalyst, ligands, solvents, and other tangible reaction conditions. Metal-catalyzed reactions of α-diazo-β-ketoesters offer great opportunity for the development of chemodivergent methodologies and have been previously explored by our group towards the synthesis of valuable synthetic intermediates such as cyclopropanes, cyclopropenes, 1,2-dihydrofuran (DHF) acetals and β,γ-unsaturated β-ketoesters. Herein, we discuss our efforts in maneuvering the reactivity of pyrrole-containing α-Diazo-β-Ketoesters towards the selective synthesis of DHF acetals and highly substituted indoles. Furthermore, we highlight how both the indoles and DHF acetals can be utilized as strategic templates for further synthetic derivatizations.

Catalyst-controlled chemodivergent reaction of α-Diazo-β-ketoesters and enol ethers: Selective synthesis of highly substituted indoles and 1,2-dihydrofuran acetals

ACS Spring Meeting 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.