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γ‐Aminoadamantanecarboxylic Acids Through Direct C–H Bond Amidations
Author(s) -
Wanka Lukas,
Cabrele Chiara,
Vanejews Maksims,
Schreiner Peter R.
Publication year - 2007
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.200600975
Subject(s) - chemistry , yield (engineering) , bromine , hydrolysis , peptide bond , amino acid , organocatalysis , bond cleavage , peptide , cleavage (geology) , peptide synthesis , combinatorial chemistry , stereochemistry , solid phase synthesis , organic chemistry , adamantane , catalysis , enantioselective synthesis , biochemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
Utilizing bromine‐free, direct C–H bond amidations we have synthesized a large variety of adamantane amides. Depending on the precursors used these amides directly yield pharmaceutically active aminoadamantanes or γ‐aminoadamantanecarboxylic acids after hydrolytic cleavage. Theserigid analogues of γ‐aminobutyric acid (GABA) were protected at the C‐ and N‐termini and we synthesized a number of peptides incorporating γ‐aminoadamantanecarboxylicacids in solution as well as via solid phase peptide synthesis. These peptides are promising scaffolds for applications in medicinal chemistry as well as in organocatalysis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)