62214-39-5Relevant articles and documents
Enzymatic resolution of 1,1-dimethoxybut-3-en-2-ol and 1,1-dimethoxypent-4- en-2-ol, α-hydroxyaldehyde precursors for aldol-type reactions
Chenevert, Robert,Gravil, Sebastien,Bolte, Jean
, p. 2081 - 2086 (2005)
Hydroxyacetals 2 and 3 were resolved by acylation with vinyl acetate in the presence of lipases in organic media. The reverse reaction, the enzymatic hydrolysis of the corresponding acetates, was also highly stereoselective and provided the opposite enant
The Role of Trichloroacetimidate to Enable Iridium-Catalyzed Regio- And Enantioselective Allylic Fluorination: A Combined Experimental and Computational Study
Sorlin, Alexandre M.,Mixdorf, Jason C.,Rotella, Madeline E.,Martin, Robert T.,Gutierrez, Osvaldo,Nguyen, Hien M.
supporting information, p. 14843 - 14852 (2019/10/11)
Asymmetric allylic fluorination has proven to be a robust and efficient methodology with potential applications for the development of pharmaceuticals and practical synthesis for 18F-radiolabeling. A combined computational (dispersion-corrected
Asymmetric Hydroformylation of 4-Vinyl-1,3-dioxolan-2-one
Pongrácz, Péter,Kollár, László
, p. 1430 - 1436 (2017/03/27)
A chiral cyclic carbonate, 4-vinyl-1,3-dioxolan-2-one was used as racemic substrate in asymmetric hydroformylation. The catalysts were formed in situ from “pre-formed” PtCl2(diphosphine) and tin(II) chloride. (2S,4S)-2,4-Bis(diphenylphosphinopentane ((S,S)-BDPP)), (S,S)-2,3-O-izopropylidine-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane ((S,S)-DIOP)), and (R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ((R)-BINAP)) were used as optically active diphosphine ligands. The platinum-containing catalytic systems provided surprisingly high activity. The hydroformylation selectivities of up to 97% were accompanied by perfect regioselectivity towards the dioxolane-based linear aldehyde. The enantiomeric composition of all components in the reaction mixture was determined and followed throughout the reaction. The unreacted 4-vinyl-1,3-dioxolan-2-one was recovered in optically active form. The kinetic resolution was rationalized using the enantiomeric composition of the substrate and the products.
Synthesis and stereospecificity of 4,5-disubstituted oxazolidinone ligands binding to T-box riboswitch RNA
Orac, Crina M.,Zhou, Shu,Means, John A.,Boehm, David,Bergmeier, Stephen C.,Hines, Jennifer V.
scheme or table, p. 6786 - 6795 (2011/12/04)
The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.
