4759-75-5Relevant academic research and scientific papers
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.
An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones
Chaubey, Narendra,Date, Sonali M.,Ghosh, Sunil K.
experimental part, p. 2721 - 2730 (2009/04/07)
The asymmetric desymmetrization of 3-substituted glutaric anhydrides 1 bearing silyl, aryl and alkyl groups with the lithium salt of chiral oxazolidin-2-ones has been studied. The effects of the substituents at the 4- and 5-positions of the oxazolidin-2-ones on the diastereoselectivity of the anhydride opening were studied in detail. A SuperQuat chiral oxazolidin-2-one 2e with 5,5-diaryl substituents showed optimum selectivity.
Enzymatic desymmetrization of 3-arylglutaric acid anhydrides
Fryszkowska, Anna,Komar, Marta,Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 2475 - 2485 (2007/10/03)
Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4.
