Theoretical insights into the regioselectivity of a Pictet-Spengler reaction: transition state structures leading to salsolinol and isosalsolinol
The 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.
Artículo de publicación ISI
Quote ItemJournal of Physical Organic Chemistry, 30 (8): e3666
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