Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides.

doi:10.1021/acs.orglett.9b00938

Paper

Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides.

Published Apr 9, 2019 · Moriana K. Haj, S. Banik, E. Jacobsen

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52

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Abstract

The enantio- and diastereoselective synthesis of 1,2-difluorides via chiral aryl iodide-catalyzed difluorination of cinnamamides is reported. The method uses HF-pyridine as a fluoride source and mCPBA as a stoichiometric oxidant to turn over catalyst, and affords compounds containing vicinal, fluoride-bearing stereocenters. Selectivity for 1,2-difluorination versus a rearrangement pathway resulting in 1,1-difluorination is enforced through anchimeric assistance from a N- tert-butyl amide substituent.

Study Snapshot

This study demonstrates the enantio- and diastereoselective synthesis of 1,2-difluorides using chiral aryl iodide-catalyzed difluorination of cinnamamides, with a N-tert-buty

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Catalytic, Enantioselective 1,2-Difluorination of Cinnamamides.

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References

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Aryl iodide-catalyzed asymmetric difluorination of -substituted styrenes occurs through multiple attractive non-covalent interactions, with chemo- and stereoselectivities mainly controlled by steric effect and nucleophil

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Chiral iodine catalysis enables stereoselective synthesis of C-O, C-C, N, and C-X bonds through oxidative transformations, offering advantages over classical metal-catalyzed oxidations.

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