Synthesis of halogenated bicyclic molecules involving Prins cyclization from aldehydes and non-conjugated diene alcohol

The reactions of aldehydes and a non-conjugated alcohol, (E)-octa-3,7-dien-1-ol, in the presence of halogen-containing reagents afforded the corresponding halogenated bicyclic molecules in good yields. The optimization, scope and limitations of the reactions as well as scale-up reactions have been examined. Quantum chemical calculations helped clarify the microscopic mechanism of a key reaction process, the introduction of a Cl atom to a bicyclic carbocation.

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

Functionalized tetrahydropyran (THP) rings are important building blocks and ubiquitous scaffolds in many natural products and active pharmaceutical ingredients (API). Among various established methods, the Prins reaction has emerged as a powerful technique in the stereoselective synthesis of the tetrahydropyran skeleton with various substituents, and the strategy has further been successfully applied in the total synthesis of bioactive macrocycles and related natural products. In this context, hundreds of valuable contributions have already been made in this area, and the present review is intended to provide the systematic assortment of diverse Prins cyclization strategies, covering the literature reports of the last twenty years (from 2000 to 2019), with an aim to give an overview on exciting advancements in this area and designing new strategies for the total synthesis of related natural products.

ZnAlMCM-41; a very ecofriendly and reusable solid acid catalyst for highly selective synthesis of 1, 3-dioxanes by Prins cyclization of olefins

Prins cyclization of styrene (SE) with paraformaldehyde (PFCHO) was conducted with mesoporous ZnAlMCM-41 catalysts for synthesis of 4-phenyl-1,3-dioxane (4-PDO) under a liquid phase heterogeneous catalytic method. For comparison study, the...

Synthesis of α-(aminoethyl)-α,β-enones via alkyne aza-Prins cyclization and their synthetic application to pyrrolidines

We developed the first synthetic method of conjugated enones via alkyne aza-Prins cyclization. The products could be converted into pyrrolidines by formal 5-endo-trig cyclization.