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Asymmetric Fluorocyclization of Difluoroalkenes with Concomitant Formation of a Trifluoromethyl Group.
Org Lett
March 2024
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Asymmetric electrophilic fluorination of difluoroalkenes remains undeveloped because of the poor reactivity of difluoroalkenes with electrophiles. However, such reactions, if feasible, are expected to be useful for the synthesis of chiral heterocyclic compounds with a trifluoromethyl group at the stereogenic center. In this Letter, we disclose the first example of asymmetric fluoroamide cyclization of difluoroalkenes using our dianionic phase-transfer catalyst.
View Article and Find Full Text PDFChiral Bis-phosphate Macrocycles for Catalytic, Efficient, and Enantioselective Electrophilic Fluorination.
Chemistry
April 2024
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Incorporation of privileged catalytic scaffolds into a macrocyclic skeleton represents an attractive strategy to furnish supramolecular catalysis systems with enzyme-mimetic cavity and multi-site cooperation. Herein we reported the synthesis, structure, binding properties and catalytic application of a series of chiral bis-phosphate macrocycles toward the challenging asymmetric electrophilic fluorination. With a large, integrated chiral cavity and two cooperative phosphate sites, these macrocycles exhibited good inclusion toward 1,4-diazabicyclo[2.
View Article and Find Full Text PDFStereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor.
Org Lett
April 2020
Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
An efficient fluorocyclization of ,-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic -oxo-fluorination occurs and is followed by an -oxo substitution reaction.
View Article and Find Full Text PDF[F]fluoro-benziodoxole: a no-carrier-added electrophilic fluorinating reagent. Rapid, simple radiosynthesis, purification and application for fluorine-18 labelling.
Chem Commun (Camb)
April 2018
Department of Organic Chemistry, Stockholm University, SE-106 91, Sweden.
Operationally simple radiosynthesis and purification of [18F]fluoro-benziodoxole was developed starting from a cyclotron produced [18F]F- precursor, [18F]TBAF, and tosyl-benziodoxole. The synthetic utility of [18F]fluoro-benziodoxole was demonstrated by electrophilic fluorocyclization of o-styrilamides proceeding with high RCC (typically 50-90%) and high molar activity (up to 396 GBq μmol-1).
View Article and Find Full Text PDFDianionic Phase-Transfer Catalyst for Asymmetric Fluoro-cyclization.
J Am Chem Soc
February 2018
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Inspired by the dicationic nature of the electrophilic fluorinating reagent, Selectfluor (1), we rationally designed a series of dicarboxylic acid precatalysts (2), which, when deprotonated, act as anionic phase-transfer catalysts for asymmetric fluorination of alkenes. Among them, 2a having the shortest linker moiety efficiently catalyzed unprecedented 6-endo-fluoro-cyclization of various allylic amides, affording fluorinated dihydrooxazine compounds with high enantioselectivity (up to 99% ee). In addition to cyclic substrates, acyclic trisubstituted alkenes underwent the reaction with good diastereoselectivity, whereas low diastereoselectivity was observed for linear disubstituted alkenes.
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