COAP‐Palladium‐Catalyzed Asymmetric Linear Allylic Alkylation of Vinyl Benzoxazinanones for Multifunctional 3,3′‐Disubstituted Oxindole Derivatives

Shen, Jun-Hao; Zhou, Sheng-Suo; Wang, Bailin; Liu, Wenkai; Wang, Zheng; Wang, Xingwang

doi:10.1002/adsc.202201404

Cited by 9 publications

(1 citation statement)

References 90 publications

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“…More recently, Wang et al illustrated an enantioselective linear‐allylic alkylation of vinyl benzoxazinones 1 with 3‐substituted oxindoles 72 via the complex of palladium with chiral oxamide‐phosphine ligand 30 developed by their group, allowing a facile access to series of optically active multifunctional 3,3’‐disubstituted oxindole derivatives 73 bearing a quaternary stereogenic center and a linear aryl amino side chain in 55–98% yields with 96–99% ee (Scheme 25). [42] Notably, the developed protocol demonstrated that the oxamide‐phosphine ligands could serve as a privileged chiral ligand to construct diverse chiral 3,3‐disubstituted oxindole compounds with various quaternary stereogenic centers, such as aza ‐, thio ‐ or all‐carbon quaternary stereogenic centers.…”

Section: Catalytic Asymmetric Reactions Of Vinyl Benzoxazinonesmentioning

confidence: 99%

Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives

et al. 2023

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Chiral aza‐heterocycles, as a sort of key frameworks of natural products et al, are deeply concerned by synthetic chemists. In recent years, catalytic asymmetric reactions of several types of zwitterionic intermediates, originating form benzoxazinone derivatives, have become a popular and efficient approach to obtain chiral aza‐heterocycles. Given that, this review attempts to summarize recent development in the field of catalytic asymmetric reactions of benzoxazinone derivatives as a powerful dipole precursors for the construction of aza‐heterocycles. In the past years, various benzoxazinone derivatives and their catalytic asymmetric reactions have been developed. Herein, this review is organized by the types of benzoxazinone derivatives and their catalytic asymmetric reactions to display their important synthetic potentials and values.

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Section: Catalytic Asymmetric Reactions Of Vinyl Benzoxazinonesmentioning

confidence: 99%

Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives

et al. 2023

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

Song,

Sun,

Wang

et al. 2024

Chemistry An Asian Journal

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

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Palladium‐Catalyzed [4+2] Cycloaddition of Vinyl Benzoxazinanones with 1,3‐Indanedione: Approach to Spiro‐Tetrahydroquinoline Scaffolds

Wei,

Tu,

et al. 2023

Eur J Org Chem

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A palladium catalyzed decarboxylative [4+2] cycloaddition of vinyl benzoxazinanones with 2‐arylidene indan‐1,3‐dione has been established, which afford a series of bioactive spiro‐tetrahydroquinolines (27 examples) in moderate to good yield (up to 87 %) with high diastereoselectivities. The synthetic utility of this reaction was demonstrated by gram‐scale synthesis. Compounds synthesized by this method potently inhibited proliferation in a panel of cancer cell lines. Particularly, the most potent compounds 3 ae, 3 ah, 3 aj and 3 fa displayed selective inhibition of MDA‐MB‐231 breast carcinoma cells with IC50 values of 1.292, 0.6118, 0.6558, 1.656 and 2.215 μM, respectively.

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COAP‐Palladium‐Catalyzed Asymmetric Linear Allylic Alkylation of Vinyl Benzoxazinanones for Multifunctional 3,3′‐Disubstituted Oxindole Derivatives

Cited by 9 publications

References 90 publications

Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives

Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives

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

Palladium‐Catalyzed [4+2] Cycloaddition of Vinyl Benzoxazinanones with 1,3‐Indanedione: Approach to Spiro‐Tetrahydroquinoline Scaffolds

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