title: Synthesis of sterically hindered N-acylated amino acids from N-carboxyanhydrides.
abstract: Sterically hindered N-acyl, gem-disubstituted amino acids are easily prepared via the addition of organometallic reagents to N-carboxyanhydrides (NCA). The process tolerates a wide variety of functional groups and allows the synthesis of amide products not readily accessible by traditional acylation chemistry. The existence of an isocyanate intermediate was established by in situ IR spectroscopy.
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich , Vladimir Prelog Weg 1-5, 8093 Zürich, Switzerland.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Schäfer
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode
mesh_terms: D000215:Acylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry; D017616:Magnesium Compounds / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry
chemical_list: D000596:Amino Acids; D000812:Anhydrides; D001965:Bromides; D007202:Indicators and Reagents; D017616:Magnesium Compounds; D009942:Organometallic Compounds; C586611:magnesium bromide; D008094:Lithium