Gold- and Platinum-Catalyzed Prins-Type [2+2+2]-Cycloadditions: From Original Methods to Applications

Dedication

Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.

Abstract

This review presents recent advancements in gold- and platinum-catalyzed [2+2+2] cyclization involving an alkyne (or an allene), an alkene, and a carbonyl compound. These transformations are referred to as Prins-type cyclization, by analogy with the classical Prins reaction, in which an alkene reacts with an oxonium species derived from a carbonyl compound. In the metal-catalyzed versions, the carbonyl engages with a metal carbene intermediate—either directly at the carbene center or at another electrophilic site within a strained ring (e.g., cyclopropane or cyclobutane)—to generate an oxonium species that reacts with an unsaturated partner to afford cyclic products. Both intra- and intermolecular variants will be discussed, along with enantioselective developments and applications toward complex molecules and natural products.

Keywords

Gold - Platinum - Atom economical process - Complex polycyclic architectures - Diastereoselective synthesis - Total synthesis - Asymmetric syntheses

Publikationsverlauf

Eingereicht: 29. Mai 2025

Angenommen nach Revision: 26. Juni 2025

Accepted Manuscript online:
26. Juni 2025

Artikel online veröffentlicht:
27. August 2025

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