Chiral Chalcogenide-Catalyzed Enantioselective Electrophilic Hydrothiolation of Alkenes

Liang, Yaoyu; Jiang, Hui; Zhang, Hang; Wang, You‐Qing; Zhao, Xiaodan

doi:10.1021/acs.orglett.2c03009

Cited by 3 publications

(3 citation statements)

References 43 publications

(29 reference statements)

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“…These catalysts can efficiently catalyze enantioselective hydrothiylation of cyclic and acyclic alkenes. In 2022, [56] they achieved enantioselective thiohydrogenation of alkenes by electrophilic pathway with succinimid‐based thioelectrophilic reagent and Et 3 SiH hydride source with the participation of catalysts 163 (Scheme 38). Similarly, the reaction goes through a process of forming a cyclothiopropane ion, which then obtains the target product with high enantioselectivity.…”

Section: Application Of Chiral Organic Selenidesmentioning

confidence: 99%

Recent Progress in Synthesis and Application of Chiral Organoselenium Compounds

Lai,

Liang,

Zeng

2024

Chemistry A European J

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Chiral organoselenium compounds have shown an important role as intermediates in many areas, such as drug discovery, organic catalysis, and nanomaterials. A lot of different methods have been developed to synthesize chiral compounds which contain selenium, because they have interesting properties and can be used in real life. Over the last few decades, a lot of progress has been made in making chiral organoselenium compounds synthetically. This work gives an overview of the progress made in creating new ways to synthesize chiral organoselenium compounds by categorizing them into groups based on the reactions they undergo. In addition, the use of chiral organoselenium compounds is also discussed.

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Section: Application Of Chiral Organic Selenidesmentioning

confidence: 99%

Recent Progress in Synthesis and Application of Chiral Organoselenium Compounds

Lai,

Liang,

Zeng

2024

Chemistry A European J

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“…Zhao and co-workers found that N -thiosuccinimides are also suitable promoters for the enantioselective hydrothiolation of alkenes at low temperatures ( Scheme 60 ) [ 91 ]. The synthesis of chiral sulfides up to 97% ee was achieved in this method.…”

Section: Reviewmentioning

confidence: 99%

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

Doraghi,

Aledavoud,

Ghanbarlou

et al. 2023

Beilstein J. Org. Chem.

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In the field of organosulfur chemistry, sulfenylating agents are an important key in C–S bond formation strategies. Among various organosulfur precursors, N-sulfenylsuccinimide/phthalimide derivatives have shown highly electrophilic reactivity for the asymmetric synthesis of many organic compounds. Hence, in this review article, we focus on the application of these alternative sulfenylating reagents in organic transformations.

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“…As an important structural unit, thioethers widely exist in natural products, drugs, , and organic functional materials . Alkenyl thioethers are a kind of sulfur-containing compounds with diverse physiological activities and unique physicochemical properties, for example, NSC 95397, prulifloxacin, methylene blue, and cefotetan (Scheme A).…”

Section: Introductionmentioning

confidence: 99%

Alkenyl Thioetherification Enabled by Nickel Catalysis

Xiang

Tan

et al. 2023

J. Org. Chem.

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This paper describes an efficient strategy to promote alkenyl thioetherifications via the Ni-catalyzed cross-coupling of inactivated or β-aryl-substituted (E)-alkenyl halides with thio-alcohols/phenols. The present strategy with easy-to-operate reaction conditions represents one of the most effective alkenyl C(sp2)–S bond-forming methods via readily accessible nickel catalysis. Notably, the mildly basic conditions employed facilitate access to a broad scope including protected amino acids, saccharides, and heterocycles. Moreover, this work presents its attractive usefulness by the application in late-stage modifications of several structurally complex natural products and pharmaceuticals.

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Chiral Chalcogenide-Catalyzed Enantioselective Electrophilic Hydrothiolation of Alkenes

Abstract: Experimental details, characterization data, HPLC traces, and NMR spectra of new compounds (PDF)Accession Codes CCDC 2015526, 2015533, and 2015539 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

Cited by 3 publications

References 43 publications

Recent Progress in Synthesis and Application of Chiral Organoselenium Compounds

Recent Progress in Synthesis and Application of Chiral Organoselenium Compounds

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

Alkenyl Thioetherification Enabled by Nickel Catalysis

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