Focused Update on the Prins Reaction and the Prins Cyclization

The Prins Reaction in the Fragrance Industry: 100th Anniversary (1919–2019)

“…The versatility of the reaction allowed for the development of numerous variations on the original Prins reaction. Amongst others, the Prins cyclization, aza‐Prins, halo‐Prins, and Prins‐pinacol reactions have been reported …”

“…The internal condensation of citronellal to form isopulegol ( 28 ) is sometime reported in the literature as an example of an intramolecular Prins reaction (Scheme ). However, when this condensation is catalyzed by a Lewis acid the mechanism follows neither a concerted mechanism (ene) nor a simple stepwise mechanism (Prins) but a more complex stepwise mechanism . Isopulegol is the precursor to one of the most industrially relevant flavor and fragrance materials, l‐menthol.…”

Effective Method of Obtaining Nopol by Prins Reaction

“…Реакция Принса представляет собой кислотнокатализируемое присоединение карбонильных соединений (преимущественно формальдегида) к алкенам [1][2][3][4][5][6][7], в результате чего возможно образование как циклических кислородсодержащих соединений (1,3-диоксан, гидрированные пираны), так и алифатических продуктов (α,β-ненасыщенные спирты, 1,3-диолы). Следует отметить, что изменение условий проведения процесса предоставляет возможность получить тот или иной желаемый продукт.…”

Structural Diversity from the Transannular Cyclizations of Natural Germacrone and Epoxy Derivatives: A Theoretical–Experimental Study

“…[53] The obtention of diketone 45 after Dess-Martin oxidation of a mixture of 43 and 44 confirmed that these two compounds are epimers at C1. However, intermediates XXIIIa and XXIIIb can further evolve, with remarkably low energetic barriers of 2.8 and 1.8 kcal mol À1 , through an intramolecular Prins reaction [54] to intermediates XXIV and XXV, which are direct precursors of compounds 43 and 44. Computational studies led us to propose the formation of aldehyde 42 and spirojatamanes 43 ( Figure 12).…”