The highly enantioselective synthesis of dihydroisoquinoline derivatives from aromatic sulfonated imines tethered with an alkyne moiety, through a one-pot asymmetric relay catalysis of chiral-phosphine and gold catalysts, is reported. Enantiomerically enriched dihydroisoquinoline derivatives were afforded in good yields and good-to-excellent ee values under mild conditions, based on the asymmetric aza-Morita-Baylis-Hillman reaction. Dihydroisoquinoline derivatives containing two chiral centers were also synthesized through further transformations.
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http://dx.doi.org/10.1002/chem.201601129 | DOI Listing |
J Fish Dis
December 2024
Escuela de Tecnología Médica, Universidad Santo Tomás, Viña del Mar, Chile.
Among the most important aquaculture resources for our country, salmon and trout stand out. Their production has increased significantly in recent decades, making them two of the most valuable resources in economic terms. However, high aquaculture production has allowed many pathogens to proliferate, causing infectious diseases and significant production losses.
View Article and Find Full Text PDFJ Inorg Biochem
October 2024
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. Electronic address:
Imine reduction is a useful reaction in the preparation of amine derivatives. Various catalysts have been reported to promote this reaction and photoredox catalysts are promising candidates for sustainable amine synthesis. Improvement of this reaction using biomolecule-based reaction scaffolds is expected to increase the utility of the reaction.
View Article and Find Full Text PDFOrg Biomol Chem
July 2024
Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, Madhya Pradesh, 462066 India.
Rhodium-catalyzed [3 + 2] annulation of diazoenals and -alkyl imines resulted in -alkyl-pyrrole-3-carbaldehyde derivatives. The reaction involves thermal 6π-electrocyclization and aromatization of a new class of enal-azomethine ylides (EAYs). The EAYs derived from dihydroisoquinoline and 2-azirine gave fused-pyrrole and pyridine derivatives, respectively.
View Article and Find Full Text PDFOrg Lett
May 2024
State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China.
The first catalytic enantioselective construction of chiral THIQUINOL and its derivatives has been accomplished through a chiral phosphoric-acid-catalyzed direct aza-Friedel-Crafts reaction of 3,4-dihydroisoquinolines with 2-naphthols/anthracen-2-ols/phenanthren-9-ol. This method offers a powerful and straightforward synthetic route toward chiral THIQUINOL derivatives with good to excellent yields and enantioselectivities. These structural motifs are crucial chiral components for further transformations into established or potential chiral ligands and catalysis.
View Article and Find Full Text PDFChem Commun (Camb)
April 2024
Key laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, 341000, China.
A pyrrolo[2,1-]isoquinoline core structure is prevalent in marine and other natural products. This article describes a tungsten-catalyzed [3+2] cycloaddition aromatization of dihydroisoquinoline ester and maleic anhydride or an acrylate. The photochemical reaction tolerates a range of functional groups such as ester, cyano, ketone, bromide, and alkene.
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