79821-75-3Relevant academic research and scientific papers
Enantiospecific synthesis of 3-pyrrolines: A route to novel polyhydroxylated pyrrolidines
Burley, Ian,Hewson, Alan T.
, p. 7099 - 7102 (2007/10/02)
Enantiomer acetamido ketones are converted by an intramolecular Wittig reaction into enantiopure 3-pyrrolines; the product from (S)-serine provides access to novel polyhydroxylated pyrrolidines.
α-Amino Acids as Chiral Educts for Asymmetric Products. Amino Acylation with N-Acylamino Acids
Buckley, Thomas F.,Rapoport, Henry
, p. 6157 - 6163 (2007/10/02)
α-N-Acylamino acids have been developed as useful reagents for the preparation of optically pure α-aminoalkylaryl ketones.Protection of the amino group as either the ethoxycarbonyl or benzenesulfonyl derivative allows alanine to serve as an effective educt for the chirally specific synthesis of a variety of structures containing the phenylethylamine backbone.Benzene undergoes Friedel-Crafts acylation with the N-acylalanine acid chloride.Catalyst complexation with oxagenated aromatics, however, prohibits acylation of aryl ethers.An arylmetallo reaction scheme overcomes this problem and also affords regiospecificity not attainable in conventional acylations.As examples, optically pure ephedrines and amphetamines were directly synthesized without recourse to resolution since the chirality of the amino acid educt was entirely conserved throughout the process.
