Abstract
Pyridyloxy-directed Rh(III)-catalyzed regioselective C3Ar-H alkenylation of protected tyrosines was achieved with N-aryl and N-alkyl maleimides, furnishing a series of maleimide-appended tyrosine-based unnatural amino acids in good yields. Further, the late-stage exemplification of the strategy was successfully accomplished on tyrosine-containing dipeptides, tripeptides, and tetrapeptides in moderate reactivity. Also, the chemical applications of the strategy were successfully executed toward nailing tyrosine with other amino acids via a maleimide linker and intramolecular hydroarylation to produce tyrosine-centered stapled products and succinimide-glued macrocyclized products, respectively.
Original language | English (US) |
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Pages (from-to) | 7673-7677 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 25 |
Issue number | 42 |
DOIs | |
State | Published - Oct 27 2023 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry