Open AccessCopper(II)-Mediated O-Arylation of Protected Serines and Threonines
Author(s) -
Mirna El Khatib,
Gary A. Molander
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol5024689
Subject(s) - chemistry , serine , threonine , stereochemistry , boronic acid , amino acid , combinatorial chemistry , biochemistry , phosphorylation
An effective protocol toward the O-arylation of β-hydroxy-α-amino acid substrates serine and threonine has been developed via Chan-Lam cross-coupling. This Cu(II)-catalyzed transformation involves benign open-flask conditions that are well-tolerated with a variety of protected (Boc-, Cbz-, Tr-, and Fmoc-) serine and threonine derivatives and various potassium organotrifluoroborates and boronic acids.
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