Novel syntheses of chiral beta- and gamma-amino acid derivatives utilizing N-protected (aminoacyl)benzotriazoles from aspartic and glutamic acids.
Friedel-Crafts reactions of N-protected (alpha-aminoacyl)benzotriazoles with hetero- and benzenoid- aromatics give alpha-amino ketones that can be reduced by either triethyl silane or sodium borohydride to form the corresponding beta- and gamma-amino acid derivatives. The preservation of chirality throughout this process is confirmed by chiral HPLC results.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Tao
Hui
H
Jiang
Rong
R
Suzuki
Kazuyuki
K
Kirichenko
Kostyantyn
K
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001224:Aspartic Acid / Q000737:chemistry*; D018698:Glutamic Acid / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
D000596:Amino Acids; D014230:Triazoles; D001224:Aspartic Acid; D018698:Glutamic Acid; C012771:benzotriazole