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Negishi Cross‐Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers
Author(s) -
Dachwitz Steffen,
Scharkowski Bjarne,
Sewald Norbert
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103353
Subject(s) - negishi coupling , structural isomer , tryptophan , chemistry , alkyl , alkylation , combinatorial chemistry , peptide , stereochemistry , amino acid , organic chemistry , catalysis , biochemistry
Mild transition‐metal catalysed cross‐couplings enable direct functionalisation of biocatalytically halogenated tryptophans with alkyl iodides, representing a new alternative for late‐stage derivatisations of halogenated aromatic amino acids. Moreover, this strategy enables preparation of (homo)tryptophan regioisomers in a simple two‐step synthesis using a Pd‐catalysed Negishi cross coupling. This method provides access to non‐canonical constitutional surrogates of tryptophan, ready for use in peptide synthesis.