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Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Bronsted Acid Catalysis.
(American Chemical Society, 2021-11-19)
[EN]Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the ...
Switchable Brønsted Acid-Catalyzed Ring Contraction of Cyclooctatetraene Oxide Towards the Enantioselective Synthesis of Cycloheptatrienyl-Substituted Homoallylic Alcohols and Oxaborinanes
(Wiley, 2023-04)
The ability of cyclooctatetraene oxide to undergo two sequential ring contraction events under mild conditions, using Brønsted acid catalysis, has been studied in detail. We have found that the selectivity can be controlled ...
Organocatalytic Enantioselective Vinylcyclopropane-Cyclopentene (VCP-CP) Rearrangement
(Wiley, 2023-05)
We have demonstrated that the catalytic and enantioselective vinylcyclopropane-cyclopentene rearrangement can be carried out on (vinylcyclopropyl)acetaldehydes through activation via enamine intermediates. The reaction ...
Mechanistic Insights in the Mode of Action of Bifunctional Pyrrolidine-Squaramide-derived Organocatalysts
(Wiley-VCH, 2016)
The modes of catalytic action of three squaramide-derived
bifunctional organocatalysts have been investigated using DFT
methods. The [5+2] cycloaddition between oxidopyrilium ylides and
enals has been used as model ...
Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
(American Chemical Society, 2016-03-18)
An easy and straightforward procedure has been developed for the synthesis of highly enantioenriched pyrrolo-[1,2-a]quinolines through a one-pot process that comprises a domino cyclopropane ring opening/aza-Michael/aldol ...
Asymmetric Dual Enamine Catalysis/Hydrogen Bonding Activation
(MDPI, 2023-07-11)
Asymmetric enamine base activation of carbonyl compounds is a well-known and widely used strategy for providing functionalization of organic compounds in an efficient way. The use of solely organic substances, which in ...
Organocatalytic Transannular Approach to Stereodefined Bicyclo[3.1.0]hexanes
(American Chemical Society, 2018-03-12)
A diastereodivergent approach to highly substituted bicyclo[3.1.0]hexanes has been developed through a transannular alkylation reaction that builds up the bicyclic core employing asymmetric organocatalysis as the tool for ...
Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family
(MDPI, 2022-01-08)
An approximation to the synthesis of several sesquiterpenes from the Guaiane family is described in which the core structure was obtained through a transannular Morita-Baylis-Hillman reaction performed under kinetic ...
Absence of Intermediates in the BINOL-Derived Mg(II)/Phosphate-Catalyzed Desymmetrizative Ring Expansion of 1-Vinylcyclobutanols
(American Chemical Society, 2021-12)
[EN] The catalyzed desymmetrizative ring expansion of alkenylcyclobutanols promoted by halofunctionalization of the alkene moiety with Nbromosuccinimide has been experimentally and computationally studied. The reaction ...
Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/ Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights
(Royal Society of Chemistry, 2017-04-01)
2-Hydroxydihydropyran-5-ones behave as excellent polyfunctional reagents able to react with enals through oxa-Michael/Michael process cascade under the combination of iminium and enamine catalysis. These racemic hemiacetalic ...