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- W4387472988 abstract "Fluorinated amino acids and related peptides/proteins have been found widespread applications in pharmaceutical and agricultural compounds. However, strategies for introducing a C-F bond into amino acids in an enantioselective manner are still limited and no such asymmetric catalysis strategy has been reported. Herein, we have successfully developed a Pd/Cu/Li ternary system for stereodivergent synthesis of chiral fluorinated amino acids. This method involves a sequential desymmetrization of geminal difluoromethylenes and allylic substitution with amino acid Schiff bases via Pd/Li and Pd/Cu dual activation, respectively. A series of non-natural amino acids bearing a chiral allylic/benzylic fluorine motif are easily synthesized in high yields with excellent regio-, diastereo-, and enantioselectivities (up to >20:1 dr and >99% ee). A density functional theory (DFT) study revealed the F-Cu interaction of the allylic substrate and the Cu catalyst significantly influence the stereoselectivity." @default.
- W4387472988 created "2023-10-11" @default.
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- W4387472988 date "2023-10-10" @default.
- W4387472988 modified "2023-10-16" @default.
- W4387472988 title "Desymmetrization of Geminal Difluoromethylenes using a Palladium/Copper/Lithium Ternary System for the Stereodivergent Synthesis of Fluorinated Amino Acids" @default.
- W4387472988 doi "https://doi.org/10.1002/anie.202313838" @default.
- W4387472988 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37815160" @default.
- W4387472988 hasPublicationYear "2023" @default.
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