%0 Journal Article %1 RN343 %A Almodovar, I. %A Rezende, M.C. %A Cassels, B.K. %A Garcia-Arriagada, M. %D 2017 %J Journal of Physical Organic Chemistry %K (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, %N 8 %R 10.1002/poc.3666 %T Theoretical Insights into the Regioselectivity of a Pictet-Spengler Reaction: Transition State Structures Leading to Salsolinol and Isosalsolinol %U /brokenurl#<Go to ISI>://WOS:000406979900005 %V 30 %X 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.

@article{RN343, 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.}, added-at = {2019-12-04T03:57:35.000+0100}, author = {Almodovar, I. and Rezende, M.C. and Cassels, B.K. and Garcia-Arriagada, M.}, biburl = {https://www.bibsonomy.org/bibtex/2cabe8724c14eea8b1c1a4867132c800d/dqcauchile}, doi = {10.1002/poc.3666}, interhash = {bc4908e5f4f1d548d411aeb4b1062fbc}, intrahash = {cabe8724c14eea8b1c1a4867132c800d}, issn = {0894-3230}, journal = {Journal of Physical Organic Chemistry}, keywords = {(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,}, number = 8, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Theoretical Insights into the Regioselectivity of a Pictet-Spengler Reaction: Transition State Structures Leading to Salsolinol and Isosalsolinol}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000406979900005}, volume = 30, year = 2017 }