A catalytic asymmetric method for the synthesis of gamma-unsaturated beta-amino acid derivatives.
Catalytic enantioselective synthesis of beta-amino acid derivatives is an area of intense interest, due to the importance of these compounds as components in pharmaceutical agents and peptidomimetics. In this report, we present the first catalytic enantioselective method for the synthesis of gamma-unsaturated beta-amino acids and their corresponding 1,3-amino alcohol derivatives. This methodology takes advantage of a highly enantioselective vinylzinc addition to an aldehyde to set chirality. The resulting allylic alcohols are then transformed into the corresponding allylic amines via Overman's [3,3]-sigmatropic imidate rearrangement, and subsequent one-pot deprotection-oxidation of a pendant oxygen leads to the gamma-unsaturated beta-amino acid derivatives of high enantiopurity.
Lurain
Alice E
AE
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA.
Walsh
Patrick J
PJ
D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
D000447:Aldehydes; D000596:Amino Acids; D009942:Organometallic Compounds; D014753:Vinyl Compounds; D015032:Zinc