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Synthesis of quaternary amino acids bearing a (2'Z)-fluorovinyl alpha-branch: potential PLP enzyme inactivators.
- Source :
-
Organic letters [Org Lett] 2004 May 27; Vol. 6 (11), pp. 1821-4. - Publication Year :
- 2004
-
Abstract
- Protected alpha-formyl amino acids, themselves available from the corresponding alpha-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinylstannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds. [structure: see text]
- Subjects :
- Amino Acids pharmacology
Aromatic-L-Amino-Acid Decarboxylases metabolism
Fluorine chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism
Sulfones chemistry
Tin Compounds chemistry
Vinyl Compounds chemical synthesis
Vinyl Compounds pharmacology
Amino Acids chemical synthesis
Amino Acids chemistry
Aromatic Amino Acid Decarboxylase Inhibitors
Vinyl Compounds chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7060
- Volume :
- 6
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 15151423
- Full Text :
- https://doi.org/10.1021/ol049422u