The use of small-molecule organic catalysts in organic synthesis has flourished over the past decade. Examples of defining concepts and cutting-edge results are provided in the papers in this Special Feature.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2996429 | PMC |
| http://dx.doi.org/10.1073/pnas.1016087107 | DOI Listing |
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Regioselective fluorination of allenes enabled by I(I)/I(III) catalysis.
Nat Commun
July 2024
Institute for Organic Chemistry, University of Münster, Corrensstraße 36, 48149, Münster, Germany.
The prominence and versatility of propargylic fluorides in medicinal chemistry, coupled with the potency of F/H and F/OH bioisosterism, has created a powerful impetus to develop efficient methods to facilitate their construction. Motivated by the well-established conversion of propargylic alcohols to allenes, an operationally simple, organocatalysis-based strategy to process these abundant unsaturated precursors to propargylic fluorides would be highly enabling: this would consolidate the bioisosteric relationship that connects propargylic alcohols and fluorides. Herein, we describe a highly regioselective fluorination of unactivated allenes based on I(I)/I(III) catalysis in the presence of an inexpensive HF source that serves a dual role as both nucleophile and Brønsted acid activator.
View Article and Find Full Text PDFPractical Synthesis of Chiral α-Aminophosphonates with Weak Bonding Organocatalysis at ppm Loading.
J Am Chem Soc
May 2024
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, Hangzhou 310030, China.
α-Aminophosphonic acids as an important class of bioisosteres of α-amino acids demonstrate various biologically important activities. We report here the development of a highly enantioselective isomerization of α-iminophosphonates enabled by an extraordinarily efficient organocatalyst. This organocatalyst afforded a total turnover number (TON) of 20,000-1,000,000 for a wide range of α-alkyl iminophosphonates.
View Article and Find Full Text PDFRegioselective, catalytic 1,1-difluorination of enynes.
Nat Chem
November 2023
Institute for Organic Chemistry, Westfälische Wilhelms-Universität (WWU) Münster, Münster, Germany.
Fluorinated small molecules are prevalent across the functional small-molecule spectrum, but the scarcity of naturally occurring sources creates an opportunity for creative endeavour in developing routes to access these important materials. Iodine(I)/iodine(III) catalysis has proven to be particularly well-suited to this task, enabling abundant alkene substrates to be readily intercepted by in situ-generated λ-iodanes and processed to high-value (di)fluorinated products. These organocatalysis paradigms often emulate metal-based processes by engaging the π bond and, in the case of styrenes, facilitating fluorinative phenonium-ion rearrangements to generate difluoromethylene units.
View Article and Find Full Text PDFBiocompatible α-Methylenation of Metabolic Butyraldehyde in Living Bacteria.
Angew Chem Int Ed Engl
September 2023
Institute of Quantitative Biology, Biochemistry and Biotechnology, School of Biological Sciences, University of Edinburgh, Edinburgh, EH9 3FF, UK.
Small molecule organocatalysts are abundant in all living organisms. However, their use as organocatalysts in cells has been underexplored. Herein, we report that organocatalytic aldol chemistry can be interfaced with living Escherichia coli to enable the α-methylenation of cellular aldehydes using biogenic amines such as L-Pro or phosphate.
View Article and Find Full Text PDFSmall-Molecule Organocatalysis Facilitates In Situ Nucleotide Activation and RNA Copying.
J Am Chem Soc
July 2023
Howard Hughes Medical Institute, Massachusetts General Hospital, Boston, Massachusetts 02114, United States.
A key challenge in origin-of-life research is the identification of plausible conditions that facilitate multiple steps along the pathway from chemistry to biology. The incompatibility of nucleotide activation chemistry and nonenzymatic template-directed RNA copying has hindered attempts to define such a pathway. Here, we show that adding heteroaromatic small molecules to the reaction network facilitates in situ nucleotide phosphate activation under conditions compatible with RNA copying, allowing both reactions to take place in the same mixture.
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