106842-97-1Relevant articles and documents
Studies on enzymatic synthesis of chiral non-racemic 3-arylglutaric acid monoesters
Fryszkowska, Anna,Komar, Marta,Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 961 - 966 (2006)
The enantioselective enzymatic desymmetrization (EED) of various 3-arylglutaric anhydrides 1 with alcohols in organic media has been studied. The effect of the solvent on the stereochemical outcome of the reaction was investigated in detail. The amount of biocatalyst was optimized, and the possibility of its re-use was tested. The first example of the EED of 3-substituted glutaric anhydrides with esters as nucleophiles is reported.
N-Heterocyclic carbene as a Br?nsted base catalyst for the amination of naphthol derivatives and alcoholysis of glutaric anhydrides
Jayakrishnan,Tamilarasu,Jincy,Kaliyamoorthy, Alagiri
supporting information, (2019/09/30)
A non-covalent Br?nsted-basic N-heterocyclic carbene catalyzed (NHC) Friedel-Crafts type amination of naphthol derivatives using dialkyl azodicarboxylates as the aminating source and alcoholysis of various glutaric anhydrides using alcohol as pronucleophile is presented. Both of these reactions are performed in the presence of either commercially available free-carbene catalyst or in situ-generated carbene catalyst. Friedel-Crafts type amination reaction is an example of a hydroxy group facilitated amination reaction. Both reactions proceed via in situ activations of –OH group by the carbene catalyst through hydrogen bonding interaction and furnish the relevant products in moderate to excellent yields.
One-pot enzymatic desymmetrization and Ugi MCR
Fryszkowska, Anna,Frelek, Jadwiga,Ostaszewski, Ryszard
, p. 6064 - 6072 (2007/10/03)
A new approach to the synthesis of chiral peptidomimetics is reported. It combines an enzymatic desymmetrization of 3-phenylglutaric anhydrides with a subsequent Ugi multi-component reaction in a one-pot, two-step procedure. NMR and CD spectroscopy was used to assign the configurations of obtained products. Our synthetic method is very efficient and it can easily be extended to other types of multi-component reactions and can be used for the preparation of chiral peptidomimetic libraries.