A facile synthesis of 3,4-dimercaptofurans via sulfenylation of (E)-β-chlorovinyl ketones and 1,2-sulfur migration

Song, Eunsun; Kim, H. Y.; Oh, Kyungsoo

doi:10.1039/c6ob02772e

Cited by 19 publications

(3 citation statements)

References 15 publications

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“…In addition to this, when the reaction is performed in the presence of the appropriate electrophile, a diverse family of substituted allenones can be achieved. Thus, halogen electrophiles and N ‐(phenylthio)phthalimide ( 24 ) provide α,γ‐dihaloallenyl 23 a [35,36] and α,γ‐disulfenylated ketones 23 b , [37] respectively in good yields (Schemes 6b and 6c). Alternatively, the presence of aldehydes 25 builds aldol derivatives 23 c (Scheme 6d) [38] .…”

Section: Synthesis Of Allenonesmentioning

confidence: 99%

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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Conjugated and non-conjugated allenones appear as recurring motifs in organic synthesis, natural products and mechanistic investigations showing unique properties and applications. The ability of allenones to build cycles has provided a direct access to strained systems, medium-sized rings, arenes, heterocycles and complex polycycles. In addition, allenones have served as models in mechanistic investigations and catalysis. The critic compilation herein presented will provide an exhaustive overview of the synthetic possibilities allenones may offer, which certainly will inspire our community in their search of more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and improve our knowledge in theoretical organic chemistry. Great part of this review will discuss synthetic aspects, catalysis innovation and mechanistic insights of the chemical transformations implying the allenone motif. In addition, many examples on total synthesis and pharmacologically active compounds will be described. We hope that this overview will be attractive to the organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products and medicinal chemistry communities. 3.5. Synthesis of Spirocycles and Bridged Structures 3.6. Open-Chain Structures from Allenones 3.7. Allenones in Total Synthesis 4.

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Section: Synthesis Of Allenonesmentioning

confidence: 99%

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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“…Between the nitrogen or sulfur atom in TMSNCS, electrophilic attack of nitrogen on II led to thermodynamically favored product 155. In 2017, sulfenylation of (E)-β-chlorovinyl ketones 156 using N-(alkyl/arylthio)phthalimides 14 access to 3,4-dimercaptofuran skeletons 159 was presented by Kim and Oh et al (Scheme 68) [98]. In the first step, by using Et N and t-BuOK in the reaction of (E)-β-chlorovinyl ketones 156 and N-(phenylthio)phthalimide 14, a series of α,γ-dithioallenyl ketones 157 and α,α-dithiopropargyl ketones 158 were obtained in a different ratio.…”

Section: Catalyst-free Sulfenylation By N-(sulfenyl)succinimides/phth...mentioning

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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“…Along this line, it will evoke strong demands for the creative methods to access structurally diverse allenyl thioethers and their further synthetic utilization. Although immense efforts have been made on the synthesis of various allenes from many synthetic organic chemistry communities, the research concerning the preparation of allenyl thioethers, in particular, through a simple and effective approach, is relatively underdeveloped . In this context, the development of a general and robust protocol to access the important allenyl thioether scaffolds would be highly desirable.…”

Section: Introductionmentioning

confidence: 99%

CuI-Catalyzed Decarboxylative Thiolation of Propargylic Cyclic Carbonates/Carbamates to Access Allenyl Thioethers

Wang

et al. 2021

J. Org. Chem.

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The first CuI-catalyzed decarboxylative thiolation of terminal alkyne-substituted cyclic carbonates/carbamates to access allenes has been developed. A wide range of hydroxymethyl-and aminomethylcontaining allenyl thioethers were smoothly obtained in good to excellent yields under mild conditions. The copper-allenylidene intermediate among the process is crucial to the decarboxylative thiolation reaction. This method opens up a new channel to access allenyl thioether compounds.

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A facile synthesis of 3,4-dimercaptofurans via sulfenylation of (E)-β-chlorovinyl ketones and 1,2-sulfur migration

Cited by 19 publications

References 15 publications

Highlighting the Rich Chemistry of the Allenone Moiety

Highlighting the Rich Chemistry of the Allenone Moiety

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

CuI-Catalyzed Decarboxylative Thiolation of Propargylic Cyclic Carbonates/Carbamates to Access Allenyl Thioethers

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