77447-97-3Relevant academic research and scientific papers
Erythro-Directive Reduction of α-Substituted Alkanones by Means of Hydrosilanes in Acidic Media
Fujita, Makoto,Hiyama, Tamejiro
, p. 5415 - 5421 (2007/10/02)
Hydrosilane reduced α-oxy and α-amino ketones and β-keto acid derivatives in trifluoroacetic acid to afford the corresponding erythro alcohols with high diastereoselectivity.The reaction proceeded without racemization at the carbon α to the carbonyl group.The erythro-directive reduction was explained in terms of the proton-bridged Cram cyclic model and successfully applied to the synthesis of physiologically important amino alcohols such as l-ephedrine, l-methoxamine, and erythro-2-methyl-3-piperidino-1-phenylpropanol.
Amino ketones and their preparation
-
, (2008/06/13)
Amino ketone enantiomers and their direct preparation are disclosed. The ketone may be reduced to yield carbinol enantiomer which has pharmaceutical activity.
1,4-Oxazines via Intramolecular Ring Closure of β-Hydroxydiazoacetamides: Phenylalanine to Tetrahydroindeno-1,4-oxazin-3(2H)-ones
McClure, D. E.,Lumma, P. K.,Arison, B. H.,Jones, J. H.,Baldwin, J. J.
, p. 2675 - 2679 (2007/10/02)
The synthesis of the tetrahydroindeno-1,4-oxazin-3(2H)-one system from phenylalanine is described.Conversion of the intermediate vicinal amino alcohol to the 1,4-oxazine was accomplished via BF3*Et2O-catalyzed ring closure of a β-hydroxydiazoacetam
Chiral α-Amino Ketones from the Friedel-Crafts Reaction of Protected Amino Acids
McClure, D. E.,Arison, B. H.,Jones, J. H.,Baldwin, J. J.
, p. 2431 - 2433 (2007/10/02)
The Friedel-Crafts reaction employing N-methoxycarbonyl-protected α-amino acids is described.This method yields chiral α-amino ketones which can be further used to prepare doubly chiral vicinal amino alcohols.
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.
