Cyclic Sulfinamides

Dobrydnev, Alexey V.; Popova, Maria V.; Volovenko, Yulian M.

doi:10.1002/tcr.202300221

Cited by 7 publications

(3 citation statements)

References 175 publications

(446 reference statements)

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“…The unique structural frameworks allow the creation of new chemical entities (NCE) for tackling previously intractable diseases and drug-resistant pathogens. In this regard, sulfinamides 2 and their cyclic congeners, regarded as a separate class, sultims , 3 can be considered as chiral bioisosteres of carboxamides and lactams, respectively. 4…”

Section: Table 1 Synthesis Of α-Phenyl β-Enamino γ-Sultimsmentioning

confidence: 99%

“…While syntheses for sultams (cyclic sulfonamides) are relatively common, 9 sultims still have remained an underrepresented class that can be accessed through the quite limited set of synthetic strategies. 3 10 Recently we have described the synthesis of differently substituted/functionalized β-enamino γ-sultams 11 through the carbanion-mediated sulfonate (or sulfonamide) intermolecular coupling and intramolecular cyclization (CSIC) reaction. 12 Inspired by this, we assumed that the logic inherent in the above synthetic strategy can be extended to access similarly substituted/functionalized β-enamino γ-sultims.…”

Section: Table 1 Synthesis Of α-Phenyl β-Enamino γ-Sultimsmentioning

confidence: 99%

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Synthesis of α-Phenyl β-Enamino γ-Sultims: the New Horizon of the CSIC Reaction

Dobrydnev,

Chuchvera,

Tararina

et al. 2024

Synlett

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Herein, we report the novel strategy for the synthesis of 4-enamino-5-phenyl-2,3-dihydroisothiazole 1-oxides (in other words α-phenyl β-enamino γ-sultims) based on the CSIC reaction. Particularly, readily available α-amino nitriles (the Strecker products) reacted with benzyl sulfinyl chloride to give the corresponding sulfinamides, which upon treatment with excess of LiHMDS converted into the target α-phenyl β-enamino γ-sultims. The method works well and tolerates strained 3- and 4-membered spirocyclic substituents. A preliminary in silico study indicated that the γ-sultim scaffold can be considered a promising pharmacophore template.

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Section: Table 1 Synthesis Of α-Phenyl β-Enamino γ-Sultimsmentioning

confidence: 99%

Section: Table 1 Synthesis Of α-Phenyl β-Enamino γ-Sultimsmentioning

confidence: 99%

Synthesis of α-Phenyl β-Enamino γ-Sultims: the New Horizon of the CSIC Reaction

Dobrydnev,

Chuchvera,

Tararina

et al. 2024

Synlett

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“…In this scenario, a conspicuous example is that the sporadic occurrence of catalytic protocols towards chiral sulfinamides, a class of stereogenic-at-S(IV) scaffolds, which is thus difficult to fulfill the demands of systematically biological screening (Fig. 1a ) 5 – 14 . To date, the most conventional and widely employed approach for synthesizing chiral sulfinamides primarily relies on using chiral starting materials 15 – 17 or employing stoichiometric amounts of chiral auxiliaries 18 , 19 .…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic skeletal reorganization for enantioselective synthesis of S-stereogenic sulfinamides

Liu,

Fang,

et al. 2024

Nat Commun

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The enantioselective synthesis of S-stereogenic sulfinamides has garnered considerable attention due to their structural and physicochemical properties. However, catalytic asymmetric synthesis of sulfinamides still remains daunting challenges, impeding their broad application in drug discovery and development. Here, we present an approach for the synthesis of S-stereogenic sulfinamides through peptide-mimic phosphonium salt-catalyzed asymmetric skeletal reorganization of simple prochiral and/or racemic sulfoximines. This methodology allows for the facile access to a diverse array of substituted sulfinamides with excellent enantioselectivities, accommodating various substituent patterns through desymmetrization or parallel kinetic resolution process. Mechanistic experiments, coupled with density functional theory calculations, clarify a stepwise pathway involving ring-opening and ring-closing processes, with the ring-opening step identified as crucial for achieving stereoselective control. Given the prevalence of S-stereogenic centers in pharmaceuticals, we anticipate that this protocol will enhance the efficient and precise synthesis of relevant chiral molecules and their analogs, thereby contributing to advancements in drug discovery.

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Chemistry in Ukraine

Grygorenko,

Lampeka,

Chebanov

et al. 2024

The Chemical Record

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In this special issue, we highlight recent advances in chemical research by scientists in Ukraine, as well as by their compatriots and collaborators outside the country. Besides spotlighting their contributions, we see our task in fostering global partnerships and multi‐, inter‐, and trans‐disciplinary collaborations, including much‐needed co‐funded projects and initiatives. The three decades of the renewed Ukraine independence have seen rather limited integration of Ukrainian (chemical) science into global research communities. [1] At the same time, the recent surge of collaborative science initiatives between European Union (EU) and Ukraine echoes the unfolding steps towards Ukraine's full research participation to the Horizon Europe Program. This recently implemented step opens enormous possibilities for Ukrainian researchers to apply for diverse EU research grants. Moreover, a number of journal special issues and collections were launched to highlight Ukrainian chemistry (i. e., by Chemistry of Heterocyclic Compounds [2] and ChemistrySelect [3]). Other scientific initiatives include ‘European Chemistry School for Ukrainians’ [4] and ‘Kharkiv Chemical Seminar’ [5] as voluntary projects aimed at engaging Ukrainian scientists into European and international chemical research.

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Cyclic Sulfinamides

Cited by 7 publications

References 175 publications

Synthesis of α-Phenyl β-Enamino γ-Sultims: the New Horizon of the CSIC Reaction

Synthesis of α-Phenyl β-Enamino γ-Sultims: the New Horizon of the CSIC Reaction

Organocatalytic skeletal reorganization for enantioselective synthesis of S-stereogenic sulfinamides

Chemistry in Ukraine

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