370862-21-8Relevant academic research and scientific papers
trans-Benzoxanthene receptors for enantioselective recognition of amino acid derivatives
Pérez, Emilio M.,Oliva, Ana I.,Hernández, José V.,Simón, Luis,Morán, Joaquín R.,Sanz, Francisca
, p. 5853 - 5856 (2001)
Neutral cleft-type hydrogen-bonding receptors based on a trans-benzoxanthene skeleton have shown good stereoselective association towards carbamate derivatives of amino acids. Among these, the best results corresponded to the commercially available benzyloxycarbamate (Cbz) while the t-butyloxycarbamate (Boc) protecting group afforded disappointing results. Preparative TLC impregnated in ethoxycarbonyl proline provided a rapid way to resolve the receptor racemic mixture. X-Ray analysis and Overhauser effects allow us to suggest a structure for these complexes and the reasons for the observed chiral discrimination.
Enantioselective recognition of α-amino acid derivatives with a cis-tetrahydrobenzoxanthene receptor
Oliva, Ana I.,Simon, Luis,Hernandez, Jose V.,Muniz, Francisco M.,Lithgow, Anna,Jimenez, Alicia,Moran, Joaquin R.
, p. 1050 - 1052 (2002)
A cis-tetrahydrobenzoxanthene receptor has shown good enantioselective association with benzyloxycarbonyl amino acid derivatives.
Urea-tetrahydrobenzoxanthene receptors for carboxylic acids
Oliva, Ana I.,Simón, Luis,Mu?iz, Francisco M.,Sanz, Francisca,Morán, Joaquín R.
, p. 3755 - 3762 (2007/10/03)
Hydrogen-bonding receptors for carboxylic acids have been prepared based on a cis tetrahydrobenzoxanthene skeleton. X-ray diffraction study of one of these compounds revealed that the cleft is suitable for establishing strong linear hydrogen bonds with the oxygen of a water molecule. Complexes that set only three H-bonds with the guests showed no chiral recognition with amino acid derivatives. However, suitable functionalization of the receptor provided a fourth H-bond with certain amino acid derivatives, leading to significant enantioselective complexation in this case.
