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Palladium-catalyzed indium-mediated reductive aromatic C-H allylation of -benzylsulfonimides with allyl esters.
Chem Commun (Camb)
April 2023
Key Laboratory of Precision and Intelligent Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.
An unprecedented reductive aromatic C-H allylation reaction of benzyl electrophiles with allyl electrophiles has been established. A range of -benzylsulfonimides smoothly participated in the palladium-catalyzed indium-mediated reductive aromatic C-H allylation with various allyl acetates, delivering structurally diverse allyl(hetero)arenes in moderate to excellent yields with good to excellent site selectivity. The use of inexpensive allyl esters for the reductive aromatic C-H allylation of -benzylsulfonimides avoids the preparation of allyl organometallic reagents in advance and complements traditional functionalization of aromatic rings.
View Article and Find Full Text PDFDichotomous Selectivity in Indium-Mediated Aza-Barbier-Type Allylation of 2--Acetyl Glycosyl Sulfinylimines in Brine: Convenient Access to Potent Anti-Influenza Agents.
J Org Chem
March 2022
Institute of Chemistry, Academia Sinica, Taipei 11529, Taiwan.
A highly diastereoselective indium-mediated allylation of 2--acetyl glycosyl sulfinylimines in brine under mild reaction conditions is reported. The method allows the achievement of a highly remarkable dichotomous selectivity for substrates, providing a single diastereoisomer of the product in 80-98% yield. With chiral ()-homoallylic sulfinamide ()- and ()- formed as key intermediates, two potent anti-influenza agents, zanamivir and zanaphosphor, were synthesized in 50% and 41% overall yields, respectively.
View Article and Find Full Text PDFSolvent Effects on Heterogeneous Rate Constants for Indium Mediated Allylations.
J Phys Chem A
March 2021
Department of Chemistry, Hobart and William Smith Colleges, Geneva, New York 14456, United States.
Indium mediated allylation is a highly selective tool for synthetic chemists to create carbon-carbon bonds, but the first step, heterogeneous reaction of allyl halides at solid indium surfaces, is still poorly understood. For example, the nature of the solvent dramatically affects the rate of reaction, but solvent choice is often based on empirical experiments. Fundamental kinetic studies are the best way to study this effect, but the determination of heterogeneous rate constants is challenging.
View Article and Find Full Text PDFNew Methods and Strategies in the Synthesis of Terpenoid Natural Products.
Acc Chem Res
March 2021
Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
Indoloterpenoids of the paxilline type belong to a large family of secondary metabolites that exhibit unique molecular architectures and a diverse set of biological activities. More than 100 congeners identified to date share a common structural motif that contains an indole moiety fused to a rearranged diterpenoid fragment. The representative physiological and cellular effects attributed to this family of natural products include neurological and insecticidal activities, modulation of lipid balance, and inhibition of mitosis.
View Article and Find Full Text PDFTotal Synthesis of Aquayamycin.
Chemistry
December 2016
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
An efficient and practical total synthesis of aquayamycin has been accomplished. The highly oxidized and stereochemically complex tetracyclic ring system was constructed using three key reactions: 1) highly diastereoselective 1,2-addition of C-glycosyl naphthyllithium to a cyclic ketone, 2) indium-mediated site-selective allylation-rearrangement sequence of naphthoquinone, and 3) diastereoselective intramolecular pinacol coupling. This synthetic strategy offers a novel and efficient pathway to prepare aquayamycin-type angucycline antibiotics.
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