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An Expedient Method for the Umpolung Coupling of Enols with Heteronucleophiles
(Wiley, 2022-08)
[EN] In this paper, we present an unprecedented and general umpolung protocol that allows the functionalization of silyl enol ethers and of 1,3-dicarbonyl compounds with a large range of heteroatom nucleophiles, including ...
Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp(3) C-O Bonds in Cyclic Acetals
(American Chemical Society, 2022)
A dual catalytic manifold that enables site-selective functionalization of unactivated sp(3) C-O bonds in cyclic acetals with aryl and alkyl halides is reported. The reaction is triggered by an appropriate sigma*-p orbital ...
Zinc Iodide Catalyzed Synthesis of Trisubstituted Allenes from Terminal Alkynes and Ketones
(American Chemical Society, 2021-09-14)
A straightforward, user-friendly, efficient protocol for the one pot, ZnI2-catalyzed allenylation of terminal alkynes with pyrrolidine and ketones, toward trisubstituted allenes, is described. Trisubstituted allenes can ...
Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters
(American Chemical Society, 2021-11-19)
[EN]Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Calpha-branched aliphatic carboxylic acids, which proceeds through the decarboxylation ...
Manganese-Catalyzed Multicomponent Synthesis of Tetrasubstituted Propargylamines: System Development and Theoretical Study
(Wiley-VCH, 2020-07-20)
The importance of multicomponent reactions as an efficient tool in organic synthesis is widely recognized, as the need for sustainable, practical, atom- and step-economic methodologies is becoming a crucial concept in ...
Stereoselective, Ruthenium-Photocatalyzed Synthesis of 1,2-Diaminotruxinic Bis-amino Acids from 4-Arylidene-5(4H)-oxazolones
(American Chemical Society, 2022-02-10)
[EN] The irradiation of (Z)-2-phenyl-4-aryliden-5(4H)-oxazolones 1 in deoxygenated CH2Cl2 at 25 °C with blue light (465 nm) in the presence of [Ru(bpy)3](BF4)2 (5% mole ratio) as a triplet photocatalyst promotes the [2+2] ...
Synthesis of 1,2-diaminotruxinic δ-cyclobutanes by BF3-controlled [2 + 2]-photocycloaddition of 5(4H)-oxazolones and stereoselective expansion of δ-cyclobutanes to give highly substituted pyrrolidine-2,5-dicarboxylates
(Royal Society of Chemistry, 2023-04)
The irradiation of (Z)-4-arylidene-5(4H)-oxazolones 1a–1u with blue light (465 nm) in the presence of the photosensitizer [Ru(bpy)3](BF4)2 (2.5 mol%) and the Lewis acid BF3·OEt2 (2 equiv.) in deoxygenated methanol at room ...
Mechanistic studies of the palladium-catalyzed S,O-ligand promoted C–H olefination of aromatic compounds
(Royal Society of Chemistry, 2023-03)
Pd-catalyzed C–H functionalization reactions of non-directed substrates have recently emerged as an
attractive alternative to the use of directing groups. Key to the success of these transformations has
been the discovery ...
Four-Step Synthesis of (−)-4-epi-Presilphiperfolan-8α-ol by Intramolecular Iron Hydride Atom Transfer-Mediated Ketone-Alkene Coupling and Studies to Access trans-Hydrindanols with a Botryane Scaffold
(Wiley, 2023-03)
From an (R)-(+)-pulegone-derived building block that incorporates the stereo-defined tertiary carbon bearing a methyl group, as found in the targeted sesquiterpenoid, a four-step synthesis of (−)-4-epi-presilphiperfolan-8-α-ol ...
Organocatalytic Enantioselective alpha-Nitrogenation of alpha,alpha- Disubstituted Aldehydes in the Absence of a Solvent
(American Chemical Society, 2022-10)
A highly efficient enantioselective alpha-nitrogenation method of alpha,alpha-disubstituted aldehydes with azodicarboxylates promoted by a chiral carbamate-monoprotected cyclohexa-1,2diamine as organocatalyst has been ...