Recent advances for the synthesis of chiral sulfones with the sulfone moiety directly connected to the chiral center

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(19), P. 5574 - 5589

Published: Jan. 1, 2021

The recent development of strategies for the asymmetric synthesis chiral sulfones with sulfone moieties directly connected to stereocenters.

Language: Английский

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Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes

Chemical Science, Journal Year: 2021, Volume and Issue: 12(19), P. 6712 - 6718

Published: Jan. 1, 2021

A nickel-catalyzed reductive asymmetric aryl-allylation of tethered unactivated alkenes has been developed, providing diverse benzene-annulated cyclic compounds bearing a quaternary stereocenter with high regio-, E/Z- and enantio-selectivity.

Language: Английский

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Synergistic Pd/Cu catalysis for stereoselective allylation of vinylethylene carbonates with glycine iminoesters: Enantioselective access to diverse trisubstituted allylic amino acid derivatives

Green Synthesis and Catalysis, Journal Year: 2021, Volume and Issue: 2(2), P. 228 - 232

Published: April 19, 2021

We reported a synergistic Pd/Cu catalyzed enantioselective decarboxylative allylation of vinylethylene carbonates with glycine iminoesters, which provides facile access to non-proteinogenic diverse trisubstituted allylic amino acid derivatives in high yields, exclusive regioselectivities and excellent stereoselectivities. This reaction tolerates wide range γ β-aryl substituted either electron-donating or electron-withdrawing groups. Significantly, this method was proven be sufficient the gram scale synthesis chiral while retaining enantioselectivity geometric control.

Language: Английский

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Carbene-Catalyzed Enantioselective Sulfonylation of Enone Aryl Aldehydes: A New Mode of Breslow Intermediate Oxidation

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(12), P. 5441 - 5449

Published: March 11, 2022

A carbene-catalyzed sulfonylation reaction between enone aryl aldehydes and sulfonyl chlorides is disclosed. The effectively installs sulfone moieties in a highly enantioselective manner to afford sulfone-containing bicyclic lactones. chloride behaves both as an oxidant nucleophilic substrate (via its reduced form) this N-heterocyclic carbene (NHC)-catalyzed process. NHC catalyst provides activation stereoselectivity control on very remote site of aldehyde substrates. Water plays important role modulating deactivation reactivation routes that involve reactions chloride. Experimental studies DFT calculations suggest unprecedented intermediate new oxidation mode the NHC-derived Breslow are involved asymmetric reaction.

Language: Английский

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Dual Cobalt/Organophotoredox Catalysis for Diastereo- and Regioselective 1,2-Difunctionalization of 1,3-Diene Surrogates Creating Quaternary Carbon Centers

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(6), P. 3651 - 3659

Published: March 7, 2022

The synthesis of compounds having quaternary carbon centers through a catalytic stereo- and regioselective difunctionalization 2-substituted 1,3-dienes remains elusive. Here, we present dual Co/photoredox-catalyzed cascade approach that addresses this challenge using modular vinyl cyclic carbonates functioning as masked 2-aryl-1,3-diene surrogates. latter species are conveniently prepared in situ converted into nucleophilic Co(allyl) intermediates intercepted by aldehydes to afford homoallylic alcohols with ample scope reaction partners. developed protocol marks significant step forward the use structurally versatile their 1,2-hydroalkylation 1,2-dicarbofunctionalization.

Language: Английский

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Multicomponent Sulfonylation of Alkenes to Access β-Substituted Arylsulfones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3772 - 3780

Published: March 6, 2023

A novel multicomponent sulfonylation of alkenes is described for the assembly various β-substituted arylsulfones using cheap and easily available K2S2O5 as a sulfur dioxide source. Of note, procedure does not need any extra oxidants metal catalysts exhibits relatively wide substrate scope good functional group compatibility. Mechanistically, an initial arylsulfonyl radical formed involving insertion with aryl diazonium salt, followed by alkoxyarylsulfonylation or hydroxysulfonylation alkenes.

Language: Английский

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Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(25), P. 16996 - 17002

Published: June 14, 2024

A highly regio- and enantioselective hydrosulfonylation using commercially available sodium sulfinates is reported, providing the first direct asymmetric rhodium-catalyzed of allenes/alkynes to synthesize chiral allylic sulfones. Ligand screening studies demonstrated indispensable role C1-symmetric P,N-ligand (Rax,S,S)-StackPhim for achieving both high regioselecitivity (>20:1) enantioselectivity (up 97% ee). Notably, operationally simple method mild conditions allow rapid preparation sulfones with a wide scope functional groups. Moreover, use tert-butyldimethylsilyloxymethanesulfinate enables collective synthesis various sulfone derivatives after transformations protected hydroxymethyl product.

Language: Английский

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Nickel-catalyzed asymmetric reductive arylation of α-chlorosulfones with aryl halides

Chemical Science, Journal Year: 2021, Volume and Issue: 12(14), P. 5253 - 5258

Published: Jan. 1, 2021

In this work Ni-Catalyzed reductive cross-coupling between (hetero)aryl halides and racemic α-chlorosulfones to prepare enantioenriched α,α-disubstituted sulfones was demonstrated, allowing facile structural derivatization of drug precursors.

Language: Английский

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Recent Progress on the Synthesis of Chiral Sulfones

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(5), P. 1216 - 1239

Published: April 7, 2021

Abstract Chiral sulfones extensively exist in drugs, agricultural chemicals, chiral organic intermediates, and functional materials. Their importance causes the rapid development of their synthetic methods recent years. Many transition metal complex catalysts with ligands organocatalysts are adopted synthesis sulfones. Most to construct based on reduction unsaturated introduction sulfone groups into hydrocarbons. This review describes all classes asymmetric reactions for

Language: Английский

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Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications

Chemical Science, Journal Year: 2020, Volume and Issue: 11(21), P. 5481 - 5486

Published: Jan. 1, 2020

The first general example of Mo-catalyzed allylic sulfonylation tertiary electrophile provides an efficient way to forge sulfone moieties, and providing ample opportunities for further transformation through traditional Suzuki cross-coupling.

Language: Английский

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