Asymmetric Synthesis of Enantioenriched 2‐Aryl‐2,3‐Dihydrobenzofurans by a Lewis Acid Catalyzed Cyclopropanation/Intramolecular Rearrangement Sequence

Pandit, Rameshwar Prasad; Kim, Seung Tae; Ryu, Do Hyun

doi:10.1002/anie.201906954

Cited by 39 publications

(19 citation statements)

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“…To achieve green and more stepand atom-economical synthesis, the exploration of new protocols based on intermolecular reactions of readily accessible starting materials is highly desirable. 9 Oxidative [3 + 2] annulation of easily available phenols and alkenes presents an appealing strategy to assemble the 2,3-dihydrobenzofuran framework. 10 For example, the pioneering work by Swenton 11 and Chiba 12 demonstrated successful anodic cycloaddition reactions.…”

Section: Introductionmentioning

confidence: 99%

Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes

et al. 2020

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“…34 In 2019, Ryu and co-workers reported a cyclopropanation/intramolecular rearrangement initiated by the Michael addition of o-quinone methides A (Scheme 5), generated in situ from o-hydroxybenzyl alcohols, with alkyl diazoacetates for the enantioselective synthesis of 2-aryl-3,3-disubstituted DHBs containing two adjacent stereogenic centers, including a quaternary carbon atom. 35 Using a chiral oxazaborolidinium ion catalyst, the reaction furnished excellent yields (up to 95%) and excellent stereoselectivity (up to >99 ee, up to >20:1 dr).…”

Section: O-quinone Methides and O-quinonesmentioning

confidence: 98%

Recent Advances in Synthetic Strategies to 2,3-Dihydrobenzofurans

Laurita

D’Orsi²,

Chiummiento³

et al. 2020

Synthesis

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This review gives an overview on recent developments in methods for the construction of compounds with the 2,3-dihydrobenzofuran core in the period 2012 to 2019. Interest in 2,3-dihydrobenzofurans is constantly increasing. The methods are divided into intermolecular and intramolecular approaches. Intermolecular approaches are subdivided according to the parent intermediate for the key reaction, while intermolecular approaches are subdivided according by which bond is formed in the key reaction. The transformation of benzofurans to dihydrobenzofurans and other miscellaneous methods are also discussed. Approaches useful for the synthesis of natural products are emphasized.1 Introduction2 Intermolecular Approaches2.1 o-Quinone Methides and o-Quinones2.2 p-Quinone Methides and p-Quinones2.3 Nitrogen-Containing Phenols and Quinones2.4 o-Hydroxyphenylcarbonyl Derivatives and Phenols2.5 Miscellaneous3 Intramolecular Approaches3.1 O–C2 Bond Forming3.2 C2–C3 Bond Forming3.3 C3–Aryl Bond Forming3.4 O–Aryl Bond Forming4 From BF to DHB5 Rearrangements and Aromatizations

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“…1a , path a vs path b) 7 – 9 . Moreover, various [4 + 1]-cycloaddition reactions of carbene species with α,β-unsaturated carbonyl compounds 10 , in situ generated o -QMs 11 , 12 , 1,3-dienes 13 , or other functionalized alkenes 14 have been realized through different reaction pathways in the presence of corresponding metal catalysts. On the other hand, the vinyl metal carbene, which possesses two electrophilic sites, could function as 1- or 3-carbon building blocks.…”

Section: Introductionmentioning

confidence: 99%

Gold(I)-catalyzed intramolecular cyclization/intermolecular cycloaddition cascade as a fast track to polycarbocycles and mechanistic insights

et al. 2021

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Metal carbene is an active synthetic intermediate, which has shown versatile applications in synthetic chemistry. Although a variety of catalytic methods have been disclosed for the generation of carbene species from different precursors, there is an increasing demand for the development of efficient and practical approaches for the in-situ formation of metal carbene intermediates with structural diversity and unrevealed reactivity. Herein we report a gold-catalyzed cascade protocol for the assembly of polycarbocyclic frameworks in high yields under mild reaction conditions. Mechanistic studies indicate that the unique β-aryl gold-carbene species, generated via gold-promoted 6-endo-dig diazo-yne cyclization, is the key intermediate in this reaction, followed by a [4 + 2]-cycloaddition with external alkenes. In comparison to the well-documented metal carbene cycloadditions, this carbene intermediate serves as a 4-C synthon in a cycloaddition reaction. A variety of elusive π-conjugated polycyclic hydrocarbons (CPHs) with multiple substituents are readily accessible from the initially generated products by a mild oxidation procedure.

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Asymmetric Synthesis of Enantioenriched 2‐Aryl‐2,3‐Dihydrobenzofurans by a Lewis Acid Catalyzed Cyclopropanation/Intramolecular Rearrangement Sequence

Cited by 39 publications

References 100 publications

Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes

Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes

Recent Advances in Synthetic Strategies to 2,3-Dihydrobenzofurans

Gold(I)-catalyzed intramolecular cyclization/intermolecular cycloaddition cascade as a fast track to polycarbocycles and mechanistic insights

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