Asymmetric synthesis of L-azetidine-2-carboxylic acid and 3-substituted congeners--conformationally constrained analogs of phenylalanine, naphthylalanine, and leucine.
Enantiopure L-azetidine-2-carboxylic acid, the (3R)-phenyl, (3R)-naphthyl and (3S)-isopropyl analogs were prepared based on a zinc-mediated asymmetric addition of allylic halides to the camphor sultam derivative of glyoxylic acid O-benzyl oxime.
Hanessian
S
S
Department of Chemistry, Université de Montréal, Québec, Canada.
Bernstein
N
N
Yang
R Y
RY
Maguire
R
R
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D001383:Azetidinecarboxylic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D007930:Leucine / Q000737:chemistry*; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry*
D010649:Phenylalanine; D001383:Azetidinecarboxylic Acid; C059031:1-naphthylalanine; D007930:Leucine; D000409:Alanine