Enantioselective synthesis of alpha-fluorinated beta2-amino acids.
A methodology for the enantioselective synthesis of alpha-fluorinated beta2-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective fluorination and alkylation gave 7 in high diastereomeric excess (>95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta2-amino acids.
Edmonds
Michael K
MK
School of Applied Science, Christchurch Polytechnic Institute of Technology, Christchurch, New Zealand.
Graichen
Florian H M
FH
Gardiner
James
J
Abell
Andrew D
AD
D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D002264:Carboxylic Acids; D006845:Hydrocarbons, Fluorinated; D023303:Oxazolidinones