Deconjugation of dehydroamino acids: stereoselective synthesis of racemic (E)-vinylglycines.
[reaction: see text] A practical and general two-step synthesis of carbamate-protected (E)-vinylglycines from aliphatic aldehydes is reported. The key step involves the kinetic alpha-protonation of dianionic dienolates derived from dehydroamino acids.
Alexander
Paul A
PA
School of Chemistry, University of Leeds, Leeds LS2 9JT, United Kingdom.
Marsden
Stephen P
SP
Muñoz Subtil
Dulce M
DM
Reader
John C
JC
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D007202:Indicators and Reagents; C006507:vinylglycine; D005998:Glycine