1335544-65-4Relevant academic research and scientific papers
Direct Lewis Acid Catalyzed Conversion of Enantioenriched N-Acyloxazolidinones to Chiral Esters, Amides, and Acids
Stevens, Jason M.,Parra-Rivera, Ana Cristina,Dixon, Darryl D.,Beutner, Gregory L.,Delmonte, Albert J.,Frantz, Doug E.,Janey, Jacob M.,Paulson, James,Talley, Michael R.
, p. 14245 - 14261 (2019/01/03)
The identification of Yb(OTf)3 through a multivariable high-throughput experimentation strategy has enabled a unified protocol for the direct conversion of enantioenriched N-acyloxazolidinones to the corresponding chiral esters, amides, and carboxylic acids. This straightforward and catalytic method has shown remarkable chemoselectivity for substitution at the acyclic N-acyl carbonyl for a diverse array of N-acyloxazolidinone substrates. The ionic radius of the Lewis acid catalyst was demonstrated as a key driver of catalyst performance that led to the identification of a robust and scalable esterification of a pharmaceutical intermediate using catalytic Y(OTf)3.
Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols
Chachignon, Hélène,Kondrashov, Evgeniy V.,Cahard, Dominique
, p. 965 - 971 (2018/01/27)
Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).
Synthesis of α-CF3-substituted carbonyl compounds with relative and absolute stereocontrol using electrophilic CF3-transfer reagents
Matousek, Vaclav,Togni, Antonio,Bizet, Vincent,Cahard, Dominique
supporting information; experimental part, p. 5762 - 5765 (2012/01/06)
Evans-type chiral lithium imide enolates undergo diastereoselective α-trifluoromethylation with a hypervalent iodine-CF3 reagent with up to 91% combined isolated yield and 97:3 dr. The resulting isolated diastereopure products can be further transformed into valuable products without racemization.
