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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 ...
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 ...
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 ...
Carboxylates as Nucleophiles in the Enantioselective Ring-Opening of Formylcyclopropanes under IminiumIon Catalysis
(Wiley-VCH, 2018-04-12)
In this work, carboxylic acids, which are typically regarded as poor nucleophiles, are demonstrated to be competent reagents to promote the ring-opening of formylcyclopropanes after activation of the latter through iminium ...
Enantioselective Synthesis of Tropanes: Brønsted Acid Catalyzed Pseudotransannular Desymmetrization
(Wiley-VCH, 2020-02-10)
The enantioselective synthesis of tropanols has been accomplished through chiral phosphoric acid catalyzed pseudotransannular ring opening of 1-aminocyclohept-4-ene-derived epoxides. The reaction proceeds together with the ...
Catalytic enantioselective domino Michael/transannular aldol reaction under bifunctional catalysis
(Royal Society of Chemistry, 2020-09-28)
The enantioselective Michael reaction catalyzed by a bifunctional tertiary amine/squaramide has been used to trigger a Michael/transannular aldol cascade process that leads to densely substituted bicyclo[5.4.0]undecanes ...
Catalytic Enantioselective Cloke–Wilson Rearrangement
(Wiley-VCH, 2018-05-09)
Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor ...
γ-Substituted Allenic Amides in the Phosphine-Catalyzed Enantioselective Higher Order Cycloaddition with Azaheptafulvenes
(American Chemical Society, 2020-05-28)
Racemic γ-substituted allenes undergo enantioselective higher order [8 + 2]-cycloaddition with azaheptafulvenes using a chiral amino acid derived amidophosphine as catalyst, providing the corresponding azaazulenoid ...
Catalytic Enantioselective Transannular Morita–Baylis–Hillman Reaction
(American Chemical Society, 2019)
Catalytic and enantioselective approaches to transannular reactions are very limited and mostly are based on chiral Lewis acid catalyzed pericyclic reactions. In this report, we present an efficient and straightforward ...