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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 ...
Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines
(Wiley-VCH, 2018-09-02)
Highly enantioenriched, chromatographically-stable secondary allyl boronates featuring a 1,1,2,2-tetraethyl-1,2-ethanediol fragment (Epin) were obtained by kinetic resolution of their racemic mixtures. The Epin group at ...
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 ...
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 ...
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 ...
Ion-pairing catalysis in the enantioselective addition of hydrazones to N-acyldihydropyrrole derivatives
(Royal Society of Chemistry, 2018-07-16)
We have demonstrated that dihydropyrrole-based enamide derivatives can act as efficient precursors of chiral quaternary N-acyliminium salts under Brønsted acid catalysis that undergo reactions with hydrazones, the latter ...
Favoring Trienamine Activation through Unconjugated Dienals: Organocatalytic Enantioselective Remote Functionalization of Alkenes
(Wiley-VCH, 2014-01-29)
Unconjugated 2,5-dienals are more reactive substrates
than the corresponding fully conjugated a,b,g,dunsaturated
aldehydes towards organocatalytic activation
through trienamine intermediates. This difference in ...