Abstract
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.
- (s)-norlaudanosoline
- biosynthesis,
- borylation,
- calculations,
- catalyzed
- condensation,
- density-functional-approach,
- derivatives
- dft
- dopamine,
- dqcauchile
- frontier-electron
- isosalsolinol,
- mechanism,
- norcoclaurine
- of
- pictet-spengler
- regioselectivity,
- salsolinol,
- synthase,
- tautomerism,
- theory,
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