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Mild Oxidative Cleavage of 9‐BBN‐Protected Amino Acid Derivatives
Author(s) -
Ankner Tobias,
Norberg Thomas,
Kihlberg Jan
Publication year - 2015
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.201500361
Subject(s) - chemistry , moiety , amino acid , yield (engineering) , oxidative cleavage , reagent , chloroform , cleavage (geology) , side chain , combinatorial chemistry , hydroxylysine , oxidative phosphorylation , derivative (finance) , organic chemistry , stereochemistry , biochemistry , lysine , catalysis , materials science , polymer , geotechnical engineering , fracture (geology) , economics , financial economics , engineering , metallurgy
Protection of the amino acid moiety using 9‐BBN is an effective method to enable side chain manipulations in synthesis of complex amino acids. We investigated the standard, mild method for deprotection of the 9‐BBN group in methanolic chloroform, and found that it relies on a slow oxidation mediated by molecular oxygen. Building on this insight, we have developed a method that allows for a fast and selective deprotection using simple peroxy acid reagents. After Fmoc protection, products were isolated in >90 % yield for a series of amino acid derivatives, including a galactosylated derivative of hydroxylysine.