Efficient N-heterocyclic carbene-catalyzed O- to C-acyl transfer.
[reaction: see text] An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.
Thomson
Jennifer E
JE
EaStChem, School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK.
Rix
Kathryn
K
Smith
Andrew D
AD
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D006838:Hydrocarbons / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D001372:Aza Compounds; D002254:Carbonates; D006838:Hydrocarbons; D007783:Lactones; C030011:carbene; D008697:Methane