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Late‐Stage Diversification through Manganese‐Catalyzed C−H Activation: Access to Acyclic, Hybrid, and Stapled Peptides
Author(s) -
Kaplaneris Nikolaos,
Rogge Torben,
Yin Rongxin,
Wang Hui,
Sirvinskaite Giedre,
Ackermann Lutz
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812705
Subject(s) - bioorthogonal chemistry , chemistry , manganese , catalysis , racemization , combinatorial chemistry , nucleobase , stereochemistry , organic chemistry , biochemistry , click chemistry , dna
Abstract Bioorthogonal C−H allylation with ample scope was accomplished through a versatile manganese(I)‐catalyzed C−H activation for the late‐stage diversification of structurally complex peptides. The unique robustness of the manganese(I) catalysis manifold was reflected by full tolerance of sensitive functional groups, such as iodides, esters, amides, and OH‐free hydroxy groups, thereby setting the stage for the racemization‐free synthesis of C−H fused peptide hybrids featuring steroids, drug molecules, natural products, nucleobases, and saccharides.