NMR signals can be greatly enhanced, or hyperpolarised, by interactions with -hydrogen. We demonstrate here that oximes can be reversibly hyperpolarised by coordination to an iridium complex, that oxime / geometry is significant for activity, and that hyperpolarised oximes can subsequently transfer these enhanced signals through proton exchange.
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http://dx.doi.org/10.1039/d4cc03231d | DOI Listing |
Org Lett
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, People's Republic of China.
We present a versatile palladium-catalyzed glycosylation platform that enables facile access to structurally diverse N-O-linked glycosides with constantly excellent regio- and stereoselectivities. Importantly, this approach offers a broad substrate scope, low catalyst loadings, and outstanding chemoselectivity, allowing for the selective reaction of oximes/hydroximic acids over hydroxyl groups that would otherwise pose challenges in conventional glycosylation methods. The synthetic utility of this method is further exemplified through a range of synthetic transformations and late-stage modification of bioactive molecules.
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December 2024
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
-Enoxyimides are versatile and valuable synthetic synthons in modern organic synthesis and catalysis. Herein, a silver-catalyzed hydrooxyimidation of terminal alkynes that enables the synthesis of -enoxyimides, has been demonstrated. The protocol features are simple, step- and atom-efficient, scalable, and exhibit a broad scope of functional group tolerance under mild conditions.
View Article and Find Full Text PDFOrg Lett
December 2024
College of Chemistry and Chemical Engineering, Qingdao University, 308 Ningxia RoadQingdao 266071, China.
Here, we report an electrochemical approach to generate an aldoxime-substituted nitrile oxide via the activation of nitromethane. The Cu-catalyzed Huisgen reaction of this 1,3-dipole with alkynes enables successful preparation of 48 new isoxazole aldoximes, which are typically challenging to synthesize by other methods, in 52 to 97% yields with excellent regioselectivity and chemoselectivity in a single step. Moreover, 20 3,3'-bisisoxazoles are prepared from the isoxazole aldoxime products in good yields via a two-step sequence.
View Article and Find Full Text PDFJ Org Chem
November 2024
Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Azines are valuable synthons or target molecules in organic synthesis. In this work, we report that could work as a photoreductive catalyst for the N-N homocoupling of oximes in high efficiency. This therefore enabled convenient access to a large variety of azines from the corresponding aryl and alkyl ketones, as well as aryl aldehydes in up to 99% yield.
View Article and Find Full Text PDFPlant J
November 2024
Plant Biochemistry Laboratory, PLEN, University of Copenhagen, Copenhagen, Denmark.
Cytochrome P450 monooxygenases of the CYP79 family catalyze conversion of specific amino acids into oximes feeding into a variety of metabolic plant pathways. Here we present an extensive phylogenetic tree of the CYP79 family built on carefully curated sequences collected across the entire plant kingdom. Based on a monophyletic origin of the P450s, a set of evolutionarily distinct branches was identified.
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