112741-51-2Relevant academic research and scientific papers
Asymmetric syntheses of 1-aminocyclopropane-1-carboxylic acid derivatives
Williams, Robert M.,Fegley, Glenn J.
, p. 8796 - 8806 (2007/10/02)
Optically active D-erythro-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6- tetrahydro-4H-1,4-oxazin-2-one (13) can be efficiently condensed with various aldehydes via the Emmons-Horner-Wadsworth procedure to provide α,β-dehydrolacton
Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates
Williams, Robert M.,Sinclair, Peter J.,Zhai, Dongguan,Chen, Daimo
, p. 1547 - 1557 (2007/10/02)
The optically active D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) and D- and L-erythro-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) can be efficiently brominated to serve as electrophilic glycine templates for the asymmetric synthesis of amino acids.It was found that coupling to these templates can proceed with either net retention or net inversion of stereochemistry.The final deblocking to the amino acids is accomplished with either dissolving-metal reduction or catalytic hydrogenolysis.The syntheses of β-ethyl aspartic acid, norvaline, allylglycine, alanine, norleucine, homophenylalanine, p-methoxyhomophenylalanine, cyclopentylglycine, and cyclopentenylglycine and a formal synthesis of clavalanine are described.In addition, the direct asymmetric syntheses of N-t-BOC-allylglycine and N-t-BOC-cyclopentenylglycine are described.
