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.
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%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
}