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http://dx.doi.org/10.1002/anie.200353366 | DOI Listing |
J Am Chem Soc
January 2025
Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences, and TaiKang Center for Life and Medical Sciences, Wuhan University, Wuhan 430072, China.
A modular platform technology for the synthesis of α-aryl carbonyl derivatives via Borono-Catellani-type secondary alkylation of arenes is presented. This practical method features a broad substrate scope regarding aryl boronic acid catechol esters, secondary alkyl bromides, and diversified terminating reagents (e.g.
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 Lett
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 PDFJ Am Chem Soc
December 2024
College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China.
ACS Catal
September 2024
Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
Modular, catalytic, and stereoselective methods for the dicarbofunctionalization of alkenes can streamline the synthesis of chiral active pharmaceutical ingredients (APIs) and agrochemicals. However, despite the inherent attractive properties of iron as catalysts for practical pharmaceutical synthesis (i.e.
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