An intermolecular sulfenoamination reaction utilizing a stable sulfur precursor with a broad range of alkene structures is described. More importantly, these reactions proceed in a highly regio- and stereoselective manner to afford interesting heterocyclic motifs ready for biological studies. In addition, a highly regiodivergent approach to access the opposite regioisomers for styrene derivatives was also developed.
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http://dx.doi.org/10.1021/acs.orglett.7b03128 | DOI Listing |
Chempluschem
January 2025
University of Vienna, Faculty of Chemistry, Währinger Str. 17, 1090, Vienna, AUSTRIA.
The Lewis acid-catalyzed coupling of alkenes and aldehydes presents a modern, versatile synthetic alternative to classical carbonyl addition chemistry, offering exceptional regio- and stereoselectivity. In this work, we present a comprehensive computational investigation into the reaction mechanism of this transformation. Our findings confirm the occurrence of an enantioselective trans-annular [1,5]-hydride shift step and demonstrate that the enantioselectivity of the reaction arises predominantly from steric clashes between functional groups in the cyclization step.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Sichuan University - Wangjiang Campus: Sichuan University, Chemistry, 29 Wangjiang Rd, 610064, Chengdu, CHINA.
Poly(lactic-co-glycolic acid) (PLGA) has been widely employed for various biomedical applications owing to its biodegradability and biocompatibility. The discovery of the stereocomplex formation between enantiomeric alternating PLGA pairs underscored its potential as high-performance biodegradable materials with diverse material properties and biodegradability. Herein, we have established a regio- and stereoselective ring-opening polymerization approach for the synthesis of stereocomplexed isoenriched alternating PLGA from racemic methyl-glycolide (rac-MG).
View Article and Find Full Text PDFChem Sci
December 2024
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University Chengdu 610041 China +86 28 85502609.
As a class of readily available and multifunctional building blocks, the chemistry of 4-alken-2-ynyl carbonates remains to be explored. Presented herein is a palladium-catalysed cascade transformative reaction between 4-alken-2-ynyl carbonates and -functionalised activated alkenes. Achiral 1,1-bisalkyl-4-alken-2-ynyl carbonates undergo highly regioselective propargylic substitution with -hydroxyphenyl-tethered activated alkenes, and an auto-tandem vinylogous addition, unusual central-carbon Tsuji-Trost alkylation, protonation and β-H elimination process is followed to furnish fused and spirocyclic frameworks with high structural complexity.
View Article and Find Full Text PDFIn this review we have compiled multicomponent reactions (MCRs) that produce cyclic structures. We have covered articles reported since 2019 to showcase the recent advances in this area. In contrast to other available reviews on this topic, we focus specifically on MCRs with strong prospects in medicinal chemistry.
View Article and Find Full Text PDFBiotechnol Notes
December 2024
Centre for Molecular Biology, Central University of Jammu, Rahya Suchani (Bagla), Jammu & Kashmir, India.
The amidases (EC 3.5.1.
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