Focused Update on the Prins Reaction and the Prins Cyclization

Isidro      M. Pastor; Miguel      Yus

doi:10.2174/138527212800564196

Abstract

The Prins reaction and the Prins cyclization have stood out as important synthetic strategies, and here the latest advances in this topic are reviewed. Different mineral acids, Lewis acids, organic acids and supported acidic materials have been employed as promoters for this type of transformation, the reaction with paraformaldehyde being the most considered one. Without any doubt, the Prins cyclization forming oxygenated heterocycles is one of the most common tranformations, and many studies have been reported on this topic. The acid-promoted Prins cyclization of an oxocarbenium ion generated in situ from suitable starting materials in order to produce the corresponding tetrahydropyrans have been extensively studied and employed in the total synthesis of a wide number of natural products. Additionally, the Prins cyclization have been employed in the synthesis of five, seven, eight and nine membered rings. The aza version of this reaction has been also considered, the analogous aza-cyclization allowing the synthesis of piperidine derivatives, which are widely distributed in natural products.

Keywords: Prins reaction, Prins cyclization, Acid catalysis, Oxocarbenium ion, Carbon-carbon bond formation, Dehydrocoupling, dioxirane, monohydroxy derivatives, hydrophobic binding, biomimetic, RuCl3, 1-dihydroxylation, phenantryl ether (DHQ-PE)