Regioselective synthesis of methylated epigallocatechin gallate from epigallocatechin was accomplished using a 2-nitrobenzenesulfonyl (Ns) group as a protecting group for phenols. This methodology provided several methylated catechins, which are naturally scarce catechin derivatives.
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http://dx.doi.org/10.1016/j.bmcl.2009.05.111 | DOI Listing |
J Org Chem
January 2025
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China.
Pd-catalyzed C4-selective alkynylation of indoles was established by employing glycine as a transient directing group. This reaction exhibits high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse alkynylated indoles in moderate to good yields. Moreover, the readily accessible scale-up synthesis and further decorations to achieve multifunctionalized indoles demonstrate the synthetic potential of this protocol.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
The University of Manchester, School of Chemistry & Manchester Institute of Biotechnology, 131 Princess Street, M1 7DN, Manchester, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
Amide bond formation is fundamental in nature and is widely used in the synthesis of pharmaceuticals and other valuable products. Current methods for amide synthesis are often step and atom inefficient, requiring the use of protecting groups, deleterious reagents and organic solvents that create significant waste. The development of cleaner and more efficient catalytic methods for amide synthesis remains an urgent unmet need.
View Article and Find Full Text PDFOrg Lett
January 2025
Catalytic Hydrogenation Research Center, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
This work describes a chiral bifunctional squaramide/DBU sequential catalytic strategy for the enantioselective synthesis of nonfused chiral eight-membered O-heterocycles through the asymmetric addition of ynones to β,γ-unsaturated α-ketoesters followed by the regio- and diastereoselective cyclization of the adduct intermediates. Mechanistic experiments revealed that an isomerization process should be involved in the ring formation step, and the origin of the high regioselectivity and diastereoselectivity has also been elucidated by the DFT calculations.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, Uttarakhand, India.
Ni(II)-hydrazineylpyridine (Ni(II)-PyH)-catalyzed regioselective synthesis of α-benzyl substituted β-hydroxy ketones from α,β-unsaturated ketones and alcohols is reported a Fenton free-radical reaction. This protocol enables facile access to desired products in good to excellent yields in 12 h using toluene solvent at room temperature to 100 °C. The structural analysis of the products was confirmed by H, C-NMR, GC-MS, and HRMS data.
View Article and Find Full Text PDFOrg Chem Front
December 2024
Department of Chemistry, University of Pittsburgh Pittsburgh Pennsylvania 15260 USA
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