期刊
TETRAHEDRON
卷 65, 期 8, 页码 1724-1736出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.11.061
关键词
Amino acids and derivatives; Peptide analogues/mimetics
资金
- EPSRC
- Eli Lilly & Co. Ltd. (Windlesham, UK)
N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected alpha-fluoro-alpha-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, sodium glutarimide, trimethylamine and sodium azide. With single diastereoisomers; of the iodofluoroethanamide, clean inversion of configuration occurs at room temperature, but subsequent epimerisation may occur as a result of the liberated iodide. The alpha-fluoro-alpha-amino amides made underwent a wide variety of reactions depending on conditions, but in many cases the carbon-fluorine bond was compromised. However, reacting trimethylamine and N-((S)-1-phenylethyl)iodofluoroethanamide gave the corresponding alpha-fluorobetaine amide, and subsequent acidic hydrolysis led to alpha-fluorobetaine as the first example of an 'unprotected' alpha-fluoroamino acid. (C) 2008 Elsevier Ltd. All rights reserved.
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