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Copper‐Promoted O‐Arylation of the Phenol Side Chain of Tyrosine Using Triarylbismuthines
Author(s) -
Le Roch Adrien,
Hébert Martin,
Gag Alexandre
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000790
Subject(s) - chemistry , tyrosine , stereocenter , dichloromethane , side chain , tripeptide , reagent , copper , residue (chemistry) , phenol , pyridine , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , amino acid , enantioselective synthesis , catalysis , polymer , solvent
A general method for the O‐arylation of the side chain of tyrosine using triarylbismuth reagents is reported. The reaction is mediated by copper diacetate, operates at 50 °C under oxygen in dichloromethane in the presence of pyridine, shows excellent functional group compatibility, and retains the integrity of the stereogenic center. The protocol was used to arylate the tyrosine residue of dipeptides and tripeptides.