In this paper, chiral aryl iodides were used for the first time to catalyze the formation of C-O and C-N bonds of inactive olefins to obtain optically active aminolactone derivatives. The reaction is compatible with various substituted alkenyl carboxylic acid substrates. This method usually shows high activity and enantioselectivity, with a yield of up to 83% and an ee of up to 99%. It is recovery and reuse of chiral aryl iodide catalyst CIC4 showed almost no loss in product yield and enantioselectivity after 3 runs.
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http://dx.doi.org/10.1039/d4ob01575d | DOI Listing |
Org Lett
January 2025
College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.
The enantioselective synthesis of P(V)-stereogenic compounds has emerged as an interesting research topic primarily due to their significant biological activity and broad application prospects. Herein, we disclose a method for the construction of P(V)-stereogenic compounds from prochiral phosphinamides and aryl iodides via palladium- and chiral norbornene-catalyzed desymmetric annulation. The P(V)-stereogenic compounds were formed with a broad scope with excellent enantiomeric excesses.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry, IGCME, The Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
The ligand-free Lewis acid-mediated regioselective hydroamination and hydroarylation of styrenes have been successfully developed in the presence of isatins or heterocyclic aryl compounds such as benzothiophenes and benzofurans. The reactions tolerate a variety of functional groups and afford the corresponding products in moderate to good yields. Deuterium labeling experiments show that the functionalized hydrogen of styrenes was derived from the nitrogen-hydrogen of the substrates in the hydroamination.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
IISER Kolkata: Indian Institute of Science Education and Research Kolkata, Department of Chemical Sciences, Mohanpur, 741246, Nadia, INDIA.
Chiral allyl amines are important structural components in natural products, pharmaceuticals, and chiral catalysts. Herein, we report a cobalt-catalyzed enantioselective reductive coupling of imines with internal alkynes to synthesize chiral allyl amines. The reaction is catalyzed by a cobalt complex derived from commercially available bisphosphine ligand utilizing zinc as the electron donor.
View Article and Find Full Text PDFOrg Lett
January 2025
Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Shanghai Key Laboratory of New Drug Design, and School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China.
The efficient construction of chiral aryl-containing organosilicon frameworks via catalytic enantioselective three-component silylarylation of alkenes remains a great challenge. Herein, a photoredox/nickel dual-catalytic asymmetric protocol has been disclosed by using a chiral biimidazoline (BiIM) as the ligand, silylboranes as the silyl radical precursors, aryl bromides as the coupling partners, and morpholine as the promoter. Remarkably, the reaction features mild and green conditions, high reaction efficiency, and excellent enantioselectivity, enabling the facile synthesis of valuable chiral tropic acid and sila-isoflavanone structures.
View Article and Find Full Text PDFNat Chem
January 2025
Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.
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