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Stereoselective Copper-Catalyzed Cross-Coupling of α-CF-Allylboronic Acids with Diazoketones.
J Org Chem
January 2025
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.
We have studied copper-catalyzed cross-coupling of chiral α-CF-substituted allylboronic acids with α-diazoketones. The reaction proceeds with excellent regioselectivity and stereoselectivity via allylic rearrangement. The method is useful for formation a new allylic C(sp)-C(sp) bond with high selectivity.
View Article and Find Full Text PDFRegioselective Cu-Catalyzed Hydrosilylation of Internal Aryl Alkynes.
Org Lett
January 2025
Department of Chemistry, University of Tennessee, Knoxville, Knoxville, Tennessee 37996, United States.
Construction of vinylsilane building blocks is important for advancing the synthesis of complex small molecules and natural products. Herein, we report a highly regio- and stereoselective copper-catalyzed hydrosilylation of unsymmetrical internal aryl alkynes. The reaction is performed across a broad scope of internal aryl alkynes, providing exclusive access to α-vinylsilane alkenyl arene products, including several silylated small molecule drug analogs.
View Article and Find Full Text PDFBiocatalytic diversification of abietic acid in Streptomyces.
J Ind Microbiol Biotechnol
January 2025
Department of Chemistry, University of Florida, Gainesville, FL, USA.
Biocatalysis provides access to synthetically challenging molecules and commercially and pharmaceutically relevant natural product analogs while adhering to principles of green chemistry. Cytochromes P450 (P450s) are amongst the most superlative and versatile oxidative enzymes found in nature and are desired regio- and stereoselective biocatalysts, particularly for structurally complex hydrocarbon skeletons. We used 10 genome-sequenced Streptomyces strains, selected based on their preponderance of P450s, to biotransform the bioactive diterpenoid abietic acid.
View Article and Find Full Text PDFStereoselective Reaction Enabling Simultaneous Analysis of Carbon-Carbon Double-Bond Configuration and the Position of Monounsaturated Fatty Acids through UHPLC-ESI-MRM-MS.
Anal Chem
January 2025
Beijing National Laboratory for Molecular Sciences, CAS Research/Education Center for Excellence in Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, Beijing Mass Spectrum Center, Institute of Chemistry Chinese Academy of Sciences, Beijing 100190, China.
Monounsaturated fatty acids (MUFA) are an important class of nutrients and are involved in lipid metabolism. The positions of the C=C bond and cis-trans isomerism have a significant influence on their physiological activity. However, simultaneously detecting these two structural properties has been challenging due to multiple isomers of MUFA.
View Article and Find Full Text PDFMicrowave-assisted [3 + 2] cycloaddition reactions of dicyanoepoxides with benzylidene Meldrum's acids.
Org Biomol Chem
January 2025
Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman.
The [3 + 2] cycloaddition of dicyanoepoxides with benzylidene Meldrum's acid under microwave irradiation and solvent-free conditions was explored for the synthesis of trioxaspirodecanes. This method presents a highly diastereo- and regioselective route to spiro cycloadducts, delivering similar stereoselectivity to conventional reflux in toluene but with shorter reaction times and improved yields.
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