Synthesis and Transformations of NH‐Sulfoximines

Chemistry - A European Journal, Год журнала: 2021, Номер 27(69), С. 17293 - 17321

Опубликована: Сен. 14, 2021

Recent years have seen a marked increase in the occurrence of sulfoximines chemical sciences, often presented as valuable motifs for medicinal chemistry. This has been prompted by both pioneering works taking sulfoximine containing compounds into clinical trials and concurrent development powerful synthetic methods. review covers recent developments synthesis concentrating on since 2015. includes extensive S-N S-C bond formations. Flow chemistry processes are also covered. Finally, subsequent transformations sulfoximines, particularly N-functionalization reviewed, including N-S, N-P, N-C forming cyclization reactions.

Язык: Английский

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Cobalt(III)/Chiral Carboxylic Acid‐Catalyzed Enantioselective Synthesis of Benzothiadiazine‐1‐oxides via C−H Activation

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(28)

Опубликована: Май 2, 2022

Abstract Among sulfoximine derivatives containing a chiral sulfur center, benzothiadiazine‐1‐oxides are important for applications in medicinal chemistry. Here, we report that the combination of an achiral cobalt(III) catalyst and pseudo‐ C 2 ‐symmetric H 8 ‐binaphthyl carboxylic acid enables asymmetric synthesis from sulfoximines dioxazolones via enantioselective C−H bond cleavage. With optimized protocol, with several functional groups can be accessed high enantioselectivity.

Язык: Английский

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New Opportunities for the Utilization of the Sulfoximine Group in Medicinal Chemistry from the Drug Designer's Perspective**

Chemistry - A European Journal, Год журнала: 2022, Номер 28(56)

Опубликована: Июль 5, 2022

Extension of the medicinal chemistry toolbox is in vital interest drug designers. However, diffusion an innovation can be a lengthy process. Along these lines, it took almost 70 years before use sulfoximine group reached critical mass chemistry. Even though this versatile functional has increased exponentially recent years, there ample room for further innovative applications. This Review highlights emerging trends and opportunities designers utilization chemistry, such as construction complex molecules, proteolysis targeting chimeras (PROTACs), antibody-drug conjugates (ADCs) novel warheads covalent inhibition.

Язык: Английский

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The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines

Chemical Communications, Год журнала: 2022, Номер 58(72), С. 9991 - 10003

Опубликована: Янв. 1, 2022

Electrophilic aminating reagents have seen a renaissance in recent years as effective nitrogen sources for the synthesis of unprotected amino functionalities.

Язык: Английский

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Stereospecific reaction of sulfonimidoyl fluorides with Grignard reagents for the synthesis of enantioenriched sulfoximines

Chemical Communications, Год журнала: 2022, Номер 58(35), С. 5387 - 5390

Опубликована: Янв. 1, 2022

Sulfonimidoyl halides have previously shown poor stability and selectivity in reaction with organometallic reagents. Here we report the preparation of enantioenriched sulfonimidoyl fluorides their stereospecific at sulfur Grignard Notably first alkyl are prepared, including methyl. The nature N-group is important to success stereocontrolled sequence sulfoximines.

Язык: Английский

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Decarboxylative sulfoximination of benzoic acids enabled by photoinduced ligand-to-copper charge transfer

Chemical Science, Год журнала: 2022, Номер 13(45), С. 13611 - 13616

Опубликована: Янв. 1, 2022

Sulfoximines are synthetically important scaffolds and serve roles in drug discovery. Currently, there is no solution to decarboxylative sulfoximination of benzoic acids; although thoroughly investigated, limited substrate scope harsh reaction conditions still hold back traditional thermal aromatic functionalization. Herein, we realize the first acids via photo-induced ligand copper charge transfer (copper-LMCT)-enabled carbometalation. The transformation proceeds under mild conditions, has a broad scope, can be applied late-stage functionalization complex small molecules.

Язык: Английский

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Synthesis of Sulfoximines and Sulfonimidamides Using Hypervalent Iodine Mediated NH Transfer

Molecules, Год журнала: 2023, Номер 28(3), С. 1120 - 1120

Опубликована: Янв. 22, 2023

The development of NH transfer reactions using hypervalent iodine and simple sources ammonia has facilitated the synthesis sulfoximines sulfonimidamides for applications across chemical sciences. Perhaps most notably, methods have been widely applied in medicinal chemistry preparation biologically active compounds, including large-scale an API intermediate. This review provides overview these synthetic involving intermediate iodonitrene since our initial report 2016 on conversion sulfoxides into sulfoximines. covers to sulfinamides, simultaneous NH/O sulfides sulfenamides form sulfonimidamides, respectively. mechanism identification key intermediates are discussed. Developments choice reagents, reaction conditions setups used described.

Язык: Английский

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Enantioselective Synthesis of 1,2‐Benzothiazine 1‐Imines via Ru^II/Chiral Carboxylic Acid‐Catalyzed C−H Alkylation/Cyclization

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(29)

Опубликована: Май 17, 2023

Sulfondiimines are diaza-analogues of sulfones with a chiral sulfur center. Compared to and sulfoximines, their synthesis transformations have so far been studied lesser extent. Here, we report the enantioselective 1,2-benzothiazine 1-imines, i.e., cyclic sulfondiimine derivatives from sulfondiimines sulfoxonium ylides via C-H alkylation/cyclization reactions. The combination [Ru(p-cymene)Cl2 ]2 newly developed spiro carboxylic acid is key achieving high enantioselectivity.

Язык: Английский

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Rapid Access to Densely Functionalized Cyclopentenyl Sulfoximines through a Sc-Catalyzed Aza-Piancatelli Reaction

Organic Letters, Год журнала: 2024, Номер 26(2), С. 547 - 552

Опубликована: Янв. 8, 2024

Sulfoximines make up a class of compounds growing interest for crop science and medicinal chemistry, but methods directly incorporating them into complex molecular scaffolds are lacking. Here we report scandium-catalyzed variant the aza-Piancatelli cyclization that can incorporate sulfoximines as nucleophiles rather than classical aniline substrates. Starting from 2-furylcarbinols sulfoximines, reaction provides direct access to 4-sulfoximinocyclopentenones, new scaffold bearing cyclopentenone sulfoximine motifs, both bioactive compounds.

Язык: Английский

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Azasulfur(iv) derivatives of sulfite and sulfinate esters by formal S–S bond insertion of dichloramines

Chemical Science, Год журнала: 2024, Номер 15(14), С. 5333 - 5339

Опубликована: Янв. 1, 2024

Starting from N , -dichloramines and S 8 or disulfides, azasulfur( iv ) chlorides are prepared, which easily derivatised by esterification amidation. The resulting products can be converted to a variety of complex sulfur( vi compounds.

Язык: Английский

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