114937-30-3Relevant articles and documents
Manganese Catalyzed Hydrogenation of Enantiomerically Pure Esters
Widegren, Magnus B.,Clarke, Matthew L.
, p. 2654 - 2658 (2018)
A manganese-catalyzed hydrogenation of esters has been accomplished with TONs up to 1000, using cheap, environmentally benign, potassium carbonate and simple alcohols as activator and solvent, respectively. The weakly basic conditions lead to good functional group tolerance and enable the hydrogenation of enantiomerically enriched α-chiral esters with essentially no loss of stereochemical integrity.
Chemoenzymatic synthesis of antiinflammatory drugs in enantiomerically pure form
Basak, Amit,Nag, Ahindra,Bhattacharya, Gautam,Mandal, Subrata,Nag, Sikha
, p. 2403 - 2407 (2000)
A novel chemoenzymatic route to chiral antiinflammatory drugs in enantiomerically pure form is described. Copyright (C) 2000 Elsevier Science Ltd.
Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of β-Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions
Mori, Seiji,Ojima, Kohei,Oriyama, Takeshi,Sakai, Naoki
supporting information, p. 4468 - 4475 (2022/03/14)
The enantioselective kinetic resolution of β-unfunctionalized primary alcohols with benzoyl chloride was carried out in the presence of a catalytic amount of a novel chiral 1,2-diamine derived from (S)-proline. Several valuable chiral 2-substituted propan-1-ols were obtained with good enantioselectivities. Density functional theory calculations revealed that the noncovalent interaction, such as CH-πinteraction, is crucial for the enantioselectivity of the resolution. This study was conducted through an interplay between experiment and computation.
Dehydroalkylative Activation of CNN- A nd PNN-Pincer Ruthenium Catalysts for Ester Hydrogenation
He, Tianyi,Buttner, John C.,Reynolds, Eamon F.,Pham, John,Malek, Jack C.,Keith, Jason M.,Chianese, Anthony R.
supporting information, p. 17404 - 17413 (2019/11/03)
Ruthenium-pincer complexes bearing CNN- A nd PNN-pincer ligands with diethyl-or diisopropylamino side groups, which have previously been reported to be active precatalysts for ester hydrogenation, undergo dehydroalkylation on heating in the presence of tricyclohexylphosphine to release ethane or propane, giving five-coordinate ruthenium(0) complexes containing a nascent imine functional group. Ethane or propane is also released under the conditions of catalytic ester hydrogenation, and time-course studies show that this release is concomitant with the onset of catalysis. A new PNN-pincer ruthenium(0)-imine complex is a highly active catalyst for ester hydrogenation at room temperature, giving up to 15500 turnovers with no added base. This complex was shown to react reversibly at room temperature with two equivalents of hydrogen to give a ruthenium(II)-dihydride complex, where the imine functionality has been hydrogenated to give a protic amine side group. These observations have potentially broad implications for the identities of catalytic intermediates in ester hydrogenation and related transformations.
