The reaction of glycine-N-methyl amide with paraformaldehyde in the presence of ytterbium triflate (1 mol%) leads to a novel cage structure 6 which is chiral at nitrogen. Single crystal X-ray analysis and DFT calculations suggest this cage structure is rigid and adopts a single low energy conformation. Use of single enantiomer α-amino amides results in two diastereomeric tertiary amines that differ in their absolute configuration at nitrogen. These diastereoisomers interconvert under acidic conditions but are configurationally stable under basic conditions and can be readily separated by either crystallisation or column chromatography. By reacting racemic chiral α-amino amides a third diastereomeric cage can also be isolated through this re...
Abstract: Diastereomeric amide derivatives of chiral phosphorinane 8 and unprotected amino acids are...
International audienceSixteen and 24 membered aza-beta(3)-peptidic macrocycles containing a alpha-hy...
International audienceOriginal mixed selectors were synthesized by coupling a single L-valine diamid...
The reaction of glycine-N-methyl amide with paraformaldehyde in the presence of ytterbium triflate (...
International audienceThe key features that govern the chirality transfer in a structurally contract...
International audienceThe five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-t...
Asymmetric reduction of N-aryl ketimines 1a–k, 43, and 45 with trichlorosilane can be catalyzed by n...
International audienceThe synthesis of eight enantiopure molecular cages (four diastereomeric pairs ...
The orientation of a tertiary amide group adjacent to an aromatic ring may be governed by the stereo...
The successful synthesis and characterisation of a series of new chiral cages was achieved through t...
Aromatic non-natural amino acids, the outstanding feature of which was the presence of several arms,...
Chiral α-aminoxy acids of various side chains were synthesized with high optical purity starting fro...
Based on a CSD search, a meta-analysis of 1179 structures of 19 natural amino acids H3NC alpha H(R)C...
Electrophilic amination of diastereomeric 4-methoxycarbonyl pyrrolidin-2-ones allowed to prepare bot...
Abstract: Diastereomeric amide derivatives of chiral phosphorinane 8 and unprotected amino acids are...
International audienceSixteen and 24 membered aza-beta(3)-peptidic macrocycles containing a alpha-hy...
International audienceOriginal mixed selectors were synthesized by coupling a single L-valine diamid...
The reaction of glycine-N-methyl amide with paraformaldehyde in the presence of ytterbium triflate (...
International audienceThe key features that govern the chirality transfer in a structurally contract...
International audienceThe five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-t...
Asymmetric reduction of N-aryl ketimines 1a–k, 43, and 45 with trichlorosilane can be catalyzed by n...
International audienceThe synthesis of eight enantiopure molecular cages (four diastereomeric pairs ...
The orientation of a tertiary amide group adjacent to an aromatic ring may be governed by the stereo...
The successful synthesis and characterisation of a series of new chiral cages was achieved through t...
Aromatic non-natural amino acids, the outstanding feature of which was the presence of several arms,...
Chiral α-aminoxy acids of various side chains were synthesized with high optical purity starting fro...
Based on a CSD search, a meta-analysis of 1179 structures of 19 natural amino acids H3NC alpha H(R)C...
Electrophilic amination of diastereomeric 4-methoxycarbonyl pyrrolidin-2-ones allowed to prepare bot...
Abstract: Diastereomeric amide derivatives of chiral phosphorinane 8 and unprotected amino acids are...
International audienceSixteen and 24 membered aza-beta(3)-peptidic macrocycles containing a alpha-hy...
International audienceOriginal mixed selectors were synthesized by coupling a single L-valine diamid...