Recent advances in Pd-catalyzed asymmetric cyclization reactions

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 53(2), P. 883 - 971

Published: Dec. 18, 2023

This review aims to collect advancements in enantioselective palladium-catalyzed cyclization reactions over the past eleven years, and it is organized into thirteen sections depending on different types of transformations involved.

Language: Английский

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Nickel-catalysed enantioselective reaction of secondary phosphine oxides and activated vinylcyclopropanes

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(15), P. 3096 - 3100

Published: Jan. 1, 2023

Activated vinylcyclopropanes can form zwitterionic π-allylmetal species in the presence of transition metals and are widely used organic synthesis. A nickel-catalyzed asymmetric allylation secondary phosphine oxides with was described. Tertiary oxide products could be obtained up to 91% yield 92% ee.

Language: Английский

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Asymmetric [3 + 2] cycloaddition of donor–acceptor cyclopropanes with azadienes enabled by Brønsted base catalysis

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2905 - 2910

Published: Jan. 1, 2024

A chiral bifunctional Brønsted base-catalyzed enantioselective [3 + 2] cycloaddition of D–A cyclopropanes and azadienes is reported. The protocol features broad substrate scope, mild reaction conditions high functional group tolerance.

Language: Английский

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Substrate-Controlled [8 + 3] Cycloaddition of Tropsulfimides and Tropones with Zwitterionic Allenyl Palladium Species Derived from Vinylidenecyclopropane-diesters

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 4, 2024

A palladium-catalyzed regioselective [8 + 3] cycloaddition of tropsulfimides and tropones with vinylidenecyclopropane-diesters (VDCP-diesters) has been disclosed in this paper, affording decahydro-1

Language: Английский

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COAP‐Pd Catalyzed Asymmetric Formal [3+2] Cycloaddition for Optically Active Multistereogenic Spiro Cyclopentane‐Indandiones Bearing Cyclic N‐Sulfonyl Ketimine Skeletons

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(12)

Published: April 17, 2024

Abstract We reported a chiral oxamide‐phosphine ligand (COAP−Ph)‐Pd‐catalyzed asymmetric [3+2] cycloaddition reaction between vinyl cyclopropane compounds derived from 1,3‐indanedione and 2‐vinylcyclopropane‐1,1‐dicarboxylates with cyclic sulfonyl 1‐azadienes. The corresponding reactions provided series of enantiomerically active spiro cyclopentane‐indandione cyclopentane structures bearing three consecutive stereogenic centers in good yields diastereo‐ enantioselectivity. COAP−Pd complex serves not only to promote generation π ‐allyl‐palladium intermediates induce the asymmetry reaction, but also depress background reaction.

Language: Английский

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DFT Study on the Mechanism of Phosphine-Catalyzed Ring-Opening Reaction of Cyclopropyl Ketone

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

In the present study, mechanism, origin of chemoselectivity, and substituent effects phosphine-catalyzed ring-opening reaction cyclopropyl ketone have been investigated using DFT method. Multiple pathways, including formation hydrofluorenone, Cloke-Wilson product, cyclopenta-fused were studied compared. The computational results show that pathway for hydrofluorenone is most favorable one, which involves four processes: nucleophilic substitution to open three-membered ring, an intramolecular Michael addition enolate intermediate, [1,5]-proton transfer give ylide, Wittig deliver final product. For disclosing structural analysis local reactivity index performed. Moreover, also considered QTAIM analysis. current study would provide useful insights understanding chemoselective reactions.

Language: Английский

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Iron-catalyzed radical intermolecular addition of unactivated alkenes to alkenyl N-heteroarenes

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(24), P. 6973 - 6978

Published: Jan. 1, 2022

The intermolecular reductive radical coupling of olefins with alkenyl N-heteroarenes, employing an iron( iii )-catalyzed hydrogen atom transfer strategy, is described.

Language: Английский

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Nickel-Catalyzed Three-Component Alkylarylation of Alkenyl N-Heteroarenes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(46), P. 8344 - 8349

Published: Nov. 14, 2023

A nickel-catalyzed three-component alkylarylation of alkenyl N-heteroarenes with α-bromocarboxylates and aryl boronic acids is reported. The protocol provides a new method to access variety N-heteroarene substituted diarylalkanes in moderate good yields. It features mild reaction conditions, cheap nickel catalyst, readily available substrates, broad substrate scope.

Language: Английский

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Synthesis of warfarin analogs: conjugate addition reactions of alkenyl-substituted N-heterocycles with 4-hydroxycoumarin and related substrates

RSC Advances, Journal Year: 2023, Volume and Issue: 13(7), P. 4754 - 4756

Published: Jan. 1, 2023

We have developed a procedure for the Michael addition of 4-hydroxycoumarins to vinyl-substituted N-heterocycles. The chemistry is also suitable thiocoumarins and quinolinones. A mechanism proposed involving nucleophilic attack at vinyl-group protonated N-heterocycle.

Language: Английский

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Synthesis of Stereoselective Multifused Cyclic Compounds via Palladium-Catalyzed C3-Allylative Dearomatization

ACS Catalysis, Journal Year: 2023, Volume and Issue: 14(1), P. 153 - 160

Published: Dec. 12, 2023

In this study, Pd-catalyzed enantioselective C3-allylative dearomatization is performed, which proceeds via dearomative [3 + 2] cycloaddition involving quinolinium zwitterions and vinyl cyclopropanes. This protocol significant for the synthesis of complex, multifused cyclic compounds characterized by meticulously controlled multistereogenic centers using π-allyl palladium species. The method developed herein presents an approach to overcoming challenge achieving stereoselective C3-functionalization. SEGPHOS ligand plays integral role in process improving both conversion rates stereoselectivity. Our investigation also underscores versatility methodology demonstrating its potential construction stereocontrolled fused N-cyclic systems. results study lay foundation further exploration refinement asymmetric aimed at strategic N-heterocyclic compounds.

Language: Английский

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