Dynamic axial chirality of tertiary aromatic amide.. (DYNAMAX)
Dynamic axial chirality of tertiary aromatic amides, applications in asymmetric synthesis
Start date: Oct 1, 2013,
End date: Jan 20, 2016
A few years ago, the host laboratory has started a new project based on Memory of Chirality and dynamic axial chirality of tertiary aromatic amides and developed a new asymmetric synthesis of quaternary alpha-amino acids by using only the chirality of starting tertiary alpha-amino acid. The host laboratory is also currently working on the development of a new synthesis of enantioenriched non proteinogenic tertiary alpha-amino acid starting from achiral compounds (glycine and aromatic acid) and based on frozen chirality. The good results obtained encouraged them to pursue in this field. The current project consists in further extensions of these methodologies. This project is a great challenge because it is very original in terms of asymmetric synthesis, and in case of success, it would lead to the achievement of absolute asymmetric synthesis of tertiary alpha-amino acids.First, the projects plans to modify the substrates (to improve if possible the results) and then to extend these methodologies to other electrophiles in order to obtain functionalized quaternary or tertiary alpha-amino acids by aldolisation and conjugate addition. Another extension would be the application to the asymmetric synthesis of biologically active compounds, sphingophungines . Finally, the project plans to use the host laboratory expertise in the synthesis of oxazolidinone with external axial chirality to produce new chiral ligands and use them in asymmetric catalysis.
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