Synthesis of quaternary amino acids bearing a (2'Z)-fluorovinyl alpha-branch: potential PLP enzyme inactivators.
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]
Berkowitz
David B
DB
Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304, USA. dbb@unlserve.unl.edu
de la Salud-Bea
Roberto
R
Jahng
Wan-Jin
WJ
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D065105:Aromatic Amino Acid Decarboxylase Inhibitors; D001142:Aromatic-L-Amino-Acid Decarboxylases / Q000378:metabolism; D005461:Fluorine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry; D017971:Tin Compounds / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D000596:Amino Acids; D065105:Aromatic Amino Acid Decarboxylase Inhibitors; D013450:Sulfones; D017971:Tin Compounds; D014753:Vinyl Compounds; C031525:stannane; D005461:Fluorine; D001142:Aromatic-L-Amino-Acid Decarboxylases