Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene.

Autor: Ohira S; Department of Biological Chemistry, Faculty of Science, Okayama University of Science, Japan. sohira@dbc.ous.ac.jp, Akiyama M, Kamihara K, Isoda Y, Kuboki A
Jazyk: angličtina
Zdroj: Bioscience, biotechnology, and biochemistry [Biosci Biotechnol Biochem] 2002 Apr; Vol. 66 (4), pp. 887-91.
DOI: 10.1271/bbb.66.887
Abstrakt: (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C-H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone.
Databáze: MEDLINE