Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.
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http://dx.doi.org/10.1002/chem.202103318 | DOI Listing |
J Org Chem
December 2024
Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563003, P. R. China.
A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO- and ArCN-functionalized -heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH- and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions.
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December 2024
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.
Multisubstituted piperidines are prevalent units in pharmaceuticals. Herein, a photodriven anti-Markovnikov hydroaminative cyclization of a ()/()-isomeric mixture of trisubstituted alkenes using the lactate-derived -symmetric arylthiol catalyst was developed for the synthesis of -2,3-disubstituted piperidines and azepane in high diastereoselectivity and good yields. The origin of diastereoselectivity and the observed different hydroamination rate of alkene with different configurations were elucidated by the experimental and computational investigation.
View Article and Find Full Text PDFOrg Lett
December 2024
Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology (BIST), Baldiri Reixac 10, 08028 Barcelona, Spain.
Chem Commun (Camb)
December 2024
Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
J Org Chem
December 2024
Dipartimento di Chimica e Biologia "A. Zambelli", Università degli Studi di Salerno, 84084 Fisciano, SA, Italy.
Herein we report two processes facilitated by diisopropylethylamine (DIPEA) for the synthesis of novel bridged polycyclic molecule analogues to natural products. The use of 4-bromoisochroman-3-one initiated an autoxidation reaction, followed by a Diels-Alder cycloaddition in the presence of electron-deficient dienophiles. Mechanistic studies revealed isochromane-3,4-dione as a key intermediate, which undergoes in situ dienolization/dearomatization followed by a [4 + 2] cycloaddition.
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