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http://dx.doi.org/10.1021/jo951163m | DOI Listing |
J Am Chem Soc
June 2025
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
Olefins are fundamental functional groups present in numerous molecules, and the geometrical configuration of the C═C bonds often plays a critical role in determining the properties of these compounds. Alkenyl geometrical isomerization is, in principle, one of the most efficient approaches for accessing stereodefined olefins. While some progress has been made in achieving unidirectional → or → conversion via olefin geometrical isomerization, there remains a strong demand for controllable, bidirectional geometrical isomerization of C═C bonds.
View Article and Find Full Text PDFChem Commun (Camb)
April 2025
Institute of Frontier Chemistry, School of Chemical and Chemical Engineering, Shandong University, China.
Metal-catalyzed synthesis of Si-stereogenic monohydrosilanes with remote unsaturated groups remains challenging due to the potential self-overfunctionalization. Herein, we report a CuH-catalyzed enantioselective hydrosilylation of strained methylenecyclopropanes, affording various Si-stereogenic remote ()-alkenyl-substituted monohydrosilanes with high enantioselectivity. The resulting monohydrosilanes are valuable synthons, which was demonstrated by post-transformations of olefin and silane moieties.
View Article and Find Full Text PDFJ Org Chem
February 2024
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P.R. China.
A practical and efficient protocol for synthesis of >99% diastereopure - and -alkenyl nitriles is developed, through tetramethylthiourea-mediated stereospecific deoxygenation of respective - and -cyanoepoxides in ethanol. The desired products are obtained in excellent yields.
View Article and Find Full Text PDFNat Commun
November 2023
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P.R. China.
Recently, the asymmetric bifunctionalization of alkenes has received much attention. However, the development of enantioselective alkoxyalkenylation has posed a considerable challenge and has lagged largely behind. Herein, we report a new palladium-catalyzed enantioselective alkoxyalkenylation reaction, using a range of primary, secondary, and tertiary γ-hydroxy-alkenes with alkenyl halides.
View Article and Find Full Text PDFMolecules
October 2023
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China.
Selective dehydrogenative silylation is one of the most valuable tools for synthesizing organosilicon compounds. In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was firstly developed to access ()-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance. Furthermore, two pathways for RuH(CO)(PPh)/NBE-catalyzed dehydrogenative intermolecular silylation of alcohols and alkenes as well as intermolecular silylation of naphthol derivatives were investigated with HSiEt as the hydrosilane reagent.
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