A catalytic enantioselective acyloin rearrangement of acyclic aldehydes to synthesize highly optically active acyloin derivatives is described. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction provided chiral α-hydroxy aryl ketones in high yield (up to 95%) and enantioselectivity (up to 98% ee). In addition, the enantioselective acyloin rearrangement of α,α-dialkyl-α-siloxy aldehydes produced chiral α-siloxy alkyl ketones in high yield (up to 92%) with good enantioselectivity (up to 89% ee).
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http://dx.doi.org/10.1021/acs.orglett.1c00314 | DOI Listing |
J Chromatogr A
February 2025
Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei 10608 Taiwan.
Despite having identical physicochemical properties, chiral molecules require effective separation techniques due to their distinct pharmacological effects. Polysaccharide-based chiral stationary phases (CSPs) are widely used for chiral separations in liquid chromatography; however, the mechanisms of chiral recognition are not well understood. This research explored the adsorption, retention, and chiral recognition mechanisms of three amylose-based CSPs: Chiralpak ID, IF, and IG.
View Article and Find Full Text PDFMicrob Cell Fact
May 2023
The Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, Kongens Lyngby, Denmark.
J Am Chem Soc
December 2022
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, China.
The reaction of common acyl-metal species (acyl anion) with aldehydes to furnish acyloins has received much less attention and specifically was restricted to using preformed stoichiometric acyl-metal reagents. Moreover, the (catalytic) enantioselective variants remain unexplored, and the asymmetric synthesis of chiral acyloins has met significant challenges in organic synthesis. Here, we uncover the highly enantioselective coupling of acid chlorides with α-bromobenzoates by nickel catalysis for producing enantioenriched protected α-hydroxy ketones (acyloins, >60 examples) with high enantioselectivities (up to 99% ee).
View Article and Find Full Text PDFOrg Biomol Chem
November 2022
State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, And CAS Key Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China.
To date, the examples of difunctionalization of alkanes to directly incorporate two functional groups are very limited. In this study, we combined photoorgano redox catalysis and P450 biocatalysts to obtain dioxygen-functionalization of α/β-C-H bonds of arylalkanes in a straightforward manner. The synthesis of enantiomerically chiral acyloins through a one-pot two-step photoredox/P450-catalyzed cascade reaction is described.
View Article and Find Full Text PDFOrg Lett
February 2021
Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon, Jangan, Suwon 16419, Korea.
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