Enantiocontrolled synthesis of alpha-methyl amino acids via Bn2N-alpha-methylserine-beta-lactone.
[Reaction: see text] Enantiocontrolled synthesis of alpha-methyl amino acids proceeds via the regioselective organocuprate opening of Bn2N-alpha-methylserine-beta-lactone. From this chiral intermediate, a wide variety of alpha-methyl amino acids and building blocks were synthesized in excellent yields.
Smith
Nicole D
ND
Department of Chemistry, University of California, San Diego, La Jolla, California 92093, USA. smithn@uchicago.edu
Wohlrab
Aaron M
AM
Goodman
Murray
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008697:Methane / Q000737:chemistry*; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D007783:Lactones; C476502:alpha-methyl-D-serine-beta-lactone; D012694:Serine; D008697:Methane