Rhodium-Catalyzed Enal Transfer Reactions of Diazoenals: Application to Diastereoselective Synthesis of Dienal-Cyclopropanes

Dedication

This work is dedicated to Professor S. Chandrasekaran on the occasion of his 80th birthday

Abstract

Vinyl cyclopropanes are valuable functional groups in drugs or natural products as well as established precursors to trigger a rich variety of synthetic transformations. However, their reactive nature makes their installation challenging. We herein present a modular access to highly diastereoselective (>20:1) dienal-cyclopropanes from rhodium-enalcarbenoids and styrenes under mild conditions. This protocol was extended to synthesize a biologically relevant substituted pyrroline scaffold. Overall, this Rh (II)-catalyzed cyclopropanation exhibits good functional group tolerance, facile scalability, and selective access to a diverse range of dienal cyclopropane motifs featuring an all-carbon ε-quaternary stereocenter.

Keywords

Cyclopropanes - Dienalcarbenoids - Diazo compounds

Publikationsverlauf

Eingereicht: 30. September 2025

Angenommen nach Revision: 12. November 2025

Artikel online veröffentlicht:
26. November 2025

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