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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 ...
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 ...
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 ...
The Pseudotransannular Ring Opening of 1-Aminocyclohept-4-ene-derived Epoxides in the Synthesis of Tropane Alkaloids: Total Synthesis of (+/-)-Ferrugine
(Wiley, 2021-05-26)
We have optimized a synthetic approach to (+/-)-Ferrugine in 8 steps starting from 5-aminocyclohept-1-ene and using the Bronsted acid-catalyzed pseudotransannular ring-opening of the epoxide derived from this cycloheptene ...
Desymmetrization of Oxabenzonorbornadienes through Brønsted Acid-Catalyzed Enantioselective (3+2) Cycloaddition with Hydrazones
(Wiley, 2023-07)
This work presents the desymmetrization of oxabenzonorbornadienes through the (3+2) cycloaddition reaction with hydrazones using a chiral Brønsted acid such as a BINOL-derived phosphoramide. This chiral acid catalyst appears ...
Recent Advances in the Prins Reaction
(American Chemical Society, 2022-08)
The Prins reaction is a very convenient synthetic platform for the preparation of oxygen-containing heterocyclic compounds, especially tetrahydropyrans and tetrahydrofurans. While this reaction has been extensively used ...
Enantioselective transannular reactions by palladium-catalysed conjugate addition of aryl boronic acids
(Royal Society of Chemistry, 2022-05-12)
A palladium-catalyzed asymmeric conjugate addition of aryl boronic acids to medium-sized cycloalkenones followed by intramolecular aldol trapping is reported. The use of in situ formed [Pd/(QuinoxP*)] as the catalyst enables ...