A TfOH-catalyzed chemoselective [3 + 2] cycloaddition of donor-acceptor oxiranes and nitriles is described. This reaction provides an efficient and practical method for the preparation of useful 3-oxazolines in good to excellent yields (up to 99%).
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http://dx.doi.org/10.1021/acs.orglett.5b00911 | DOI Listing |
Chem
November 2024
Department of Chemistry, Brandeis University, 415 South Street, Waltham, MA 02453, USA.
We introduce donor-acceptor substituted anthracenes as effective molecular solar thermal energy storage compounds that operate exclusively in the solid state. The donor-acceptor anthracenes undergo visible light-induced [4+4] cycloaddition reaction, producing metastable cycloadducts, dianthracenes with quaternary carbons, and storing photon energy. The triggered cycloreversion of dianthracenes to anthracenes discharges the stored energy as heat in the order of 100 kJ/mol (200 J/g).
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry, University of Hyderabad, C. R. Rao Road, Gachibowli, Hyderabad 500 046, India.
A facile two-step enantiospecific synthesis of 5,6,7,8-tetrahydroindolizine scaffolds has been developed via TMSOTf-promoted [3 + 2] cycloaddition between carbohydrate-derived spirocyclic donor-acceptor cyclopropanecarboxlates and alkyl/aryl nitriles followed by an intramolecular Mitsunobu reaction of the resulting chiral 2/5-(4-hydroxybutyl)pyrrole derivatives.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, Jharkhand, 826004, India.
J Org Chem
December 2024
Department of Chemistry, University of Calcutta, 92, A. P. C. Road, Kolkata 700 009, West Bengal, India.
A series of sulfonamido-substituted oxime-ethers have been synthesized by the reaction of donor-acceptor aziridines with aldo- and keto-oximes through C-C bond cleavage. Nucleophilic attack by an oxime hydroxyl group on the -generated azomethine ylide rather than the routine cycloaddition reaction draws the novelty of the developed methodology. Selective protection of the oxime hydroxyl group is observed in the presence of phenolic -OH, which made the protocol enriched.
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