Almodovar-Fajardo, IIAlmodovar-FajardoCaroli-Rezende, MMCaroli-RezendeCassels, Bruce K.Bruce K.CasselsGarcia-Arriagada, MacarenaMacarenaGarcia-Arriagada2025-04-232025-04-23201710.1002/poc.3666https://sic.vriic.usach.cl/entities/publication/e0f78338-9824-4e0c-b600-e3d7a57f0fc6The mechanism of the cyclization step of the Pictet-Spengler reaction between acetaldehyde and dopamine to give salsolinol and isosalsolinol was studied computationally, using density functional theory. The preferential formation in acidic media of salsolinol, the product of para-cyclization, and the requirement of a neutral pH for the formation of the ortho-cyclized isosalsolinol are explained in terms of 2 different mechanistic routes with an iminium ion or a phenolate-iminium zwitterion as starting reactants. Copyright © 2016 John Wiley & Sons, Ltd.en-USDFT calculationsisosalsolinolPictet-Spengler of dopamineregioselectivitysalsolinolTheoretical Insights into the Regioselectivity of a Pictet-Spengler Reaction: Transition State Structures Leading to Salsolinol and Isosalsolinolhttps://doi.org/10.1002/poc.3666