Beilstein J. Org. Chem.2015,11, 446–468, doi:10.3762/bjoc.11.51
derivatives of many amino acids often become annoyingly strenuous due to the necessity of employing protecting groups, on one or more of the amino acid functionalities, during the synthetic sequence. However, in the case of hydroxyaminoacids such as hydroxyproline, serine, threonine, tyrosine and 3,4
-dihydroxyphenylalanine (DOPA), many O-acyl side-chain derivatives are directly accessible via a particularly expedient and scalable method not commonly applied until recently. Direct acylation of unprotected hydroxyaminoacids with acyl halides or carboxylic anhydrides under appropriately acidic reaction conditions
recognized procedure for large-scale preparation of many useful side-chain derivatives of hydroxyaminoacids and related compounds. Such derivatives are useful in peptide chemistry and drug development, as amino acid amphiphiles for asymmetric catalysis, and as amino acid acrylic precursors for preparation
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Graphical Abstract
Scheme 1:
Selective O-acetylation of hydroxyamino acids with acetic anhydride in perchloric acid-acetic acid ...