Pd-Catalyzed intermolecular asymmetric allylic dearomatization of 1-nitro-2-naphthols with MBH adducts

Zhang, Qingxia; Xie, Jiahao; Gu, Qianqun; You, Shu‐Li

doi:10.1039/d3cc00568b

Cited by 7 publications

(1 citation statement)

References 61 publications

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“…Subsequently, the Krische group reported the first example of iridium-catalyzed transfer hydrogenative C–C coupling of acrylic esters with primary alcohols to construct enantiomerically enriched 5-substituted α- exo -methylene γ-butyrolactones . In 2012, the Ding group designed and synthesized a series of chiral spiroketal-based diphosphine (SKP) ligands, which were successfully applied into Pd-catalyzed asymmetric γ-selective allylic substitution of racemic aromatic MBH adducts with a series of nucleophiles, such as aromatic amine, , β-dicarbonyl, allylboronates, and so on. , To our knowledge, the precise control over regioselectivity by chiral ligands has rarely been explored for MBH adducts involving Pd-catalyzed asymmetric allylic substitution.…”

Section: Introductionmentioning

confidence: 99%

Chiral Phosphine Ligands of COAP and SKP Switched Regiodivergent Asymmetric Allylic Alkylation of MBH Adducts

Sun,

Song,

Wang

et al. 2024

J. Org. Chem.

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The palladium-catalyzed highly regioselective asymmetric allylic alkylation of 3′-indolyl-3-oxindole derivatives with Morita−Baylis−Hillman (MBH) carbonates was developed to facilely construct chiral 3,3′-bisindole derivatives under mild reaction conditions. The regioselectivity (α/γ) of MBH carbonates was efficiently switched in the presence of chiral oxalamide phosphine or spiroketal-based diphosphine/Pd(0) complexes as a chiral catalyst. A series of multifunctional 3,3′-bisindole derivatives with allcarbon quaternary stereogenic centers were obtained in high yields with good to excellent enantio-, diastereo-, and regioselectivity. The present process is endowed with some salient features such as broad substrate scope, N-protecting group-free, excellent stereoselectivity, as well as adjustable regioselectivity.

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Section: Introductionmentioning

confidence: 99%

Chiral Phosphine Ligands of COAP and SKP Switched Regiodivergent Asymmetric Allylic Alkylation of MBH Adducts

Sun,

Song,

Wang

et al. 2024

J. Org. Chem.

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Catalytic Asymmetric Dearomative Arylation of 2‐Naphthols Enabled by o‐Quinone Diimides

Li,

Yang,

et al. 2024

Adv Synth Catal

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The catalytic asymmetric dearomative arylation of 2‐naphthols enabled by the unconventional reactivity of o‐quinone diimides, i.e. the 1,4‐conjugate addition on quinone sp2 hybridized carbon, has been etablished. Under the catalysis of chiral phosphoric acid, various cyclohexaenones bearing an all‐carbon quaternary stereocenter have been prepared with excellent yields and enantioselectivities.

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Chemo‐ and Enantioselective Intermolecular Allylation of Quinolin‐2‐ones

Li,

Wang,

Zhou

et al. 2024

Adv Synth Catal

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An enantioselective C‐, O‐ and N‐ intermolecular allylic reaction of quinolin‐2(1H)‐ones has been developed. The reaction between 3‐hydroxy quinolone and Boc‐protected MBH adducts with Pd‐catalysis provided a series of 1,4‐dihydroquinoline‐2,3‐diones in 20‐95% yield accompanied by 69‐96% enantioselectivity. In addition, the O‐allylic alkylation could occur by varying the organo‐catalyst and Boc‐protected MBH adducts from benzaldehyde. Furthermore, the N‐allylation of 3‐O‐protected quinolin‐2‐ones with allylic acetates was also realized (40‐92% yield, 78‐97% ee).

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Pd-Catalyzed intermolecular asymmetric allylic dearomatization of 1-nitro-2-naphthols with MBH adducts

Abstract: An asymmetric allylic dearomatization reaction of 1-nitro-2-naphthol derivatives with Morita-Baylis-Hillman (MBH) adducts has been developed. By utilizing Pd catalyst derived from Pd(OAc)2 and Trost ligand (R, R)-L1, the reaction proceeded...

Cited by 7 publications

References 61 publications

Chiral Phosphine Ligands of COAP and SKP Switched Regiodivergent Asymmetric Allylic Alkylation of MBH Adducts

Chiral Phosphine Ligands of COAP and SKP Switched Regiodivergent Asymmetric Allylic Alkylation of MBH Adducts

Catalytic Asymmetric Dearomative Arylation of 2‐Naphthols Enabled by o‐Quinone Diimides

Chemo‐ and Enantioselective Intermolecular Allylation of Quinolin‐2‐ones

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