Dearomative [4+2] Cycloaddition of Oxindole‐Embedded <i>ortho</i>‐Quinone Methides with 2,5‐Dialkylfurans

Shen, Yao‐Bin; Li, Shuaishuai; Liu, Xicheng; Yu, Liping; Liu, Qing; Xiao, Jian

doi:10.1002/adsc.201801509

Cited by 18 publications

(2 citation statements)

References 74 publications

(7 reference statements)

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“…Later Xiao extended this approach to the synthesis of pharmacologically important spirooxindoles by reacting 2,5-DMF with a different class of quinone-methides, the oxindoleembedded ortho-quinone-methides (Scheme 16). [34] The spiro[chroman-4,3'-oxindole] products 34 were isolate in good yields and complete diasteroselectivity (dr > 20 : 1) by using 10 mol % loading of p-toluenesulfonic acid monohydrate (p-TSA•H 2 O) as the optimal organocatalyst. The protocol can be successfully applied to a wide range of differently substituted ortho-hydroxybenzyl alcohols with respect to the electronic nature as well as the position of the substituents.…”

Section: Organocatalytic Transformations Of Dialkylfuransmentioning

confidence: 99%

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Organocatalytic Upgrading of Biomass Derived Building Blocks

Meninno

2023

Eur J Org Chem

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The depletion of finite primary fossil fuels we are facing makes necessary a deep metamorphosis in fundamental parts of the chemical industry. A progressive transition from petro‐based starting materials toward renewable biomass‐derived sources will have to take place in the synthesis of added‐value chemicals, important for our everyday life, such as pharmaceuticals, polymers, agrochemicals etc. Moreover, greener processes, carried out under friendlier reaction conditions, must be designed to address current concerns about the climate change and the resulting pressing need to reduce the environmental footprint of chemical processes. To this end, organocatalysis could offer a valuable opportunity for upgrading biomass‐derived platform molecules in line with the principles of Green Chemistry. This review presents some of recent and remarkable advancements in this emerging area. Organocatalysis has proven to be an efficient tool to transform low value bio‐based renewable platform building blocks into new high value bio‐based chemicals, with potential applications as synthetic intermediates, innovative materials and pharmaceutically active compounds.

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Section: Organocatalytic Transformations Of Dialkylfuransmentioning

confidence: 99%

“…Later Xiao extended this approach to the synthesis of pharmacologically important spirooxindoles by reacting 2,5‐DMF with a different class of quinone‐methides, the oxindole‐embedded ortho‐quinone‐methides (Scheme 16). [34] …”

Section: Organocatalytic Transformation Of Furanic Platform Molecules...mentioning

confidence: 99%

Organocatalytic Upgrading of Biomass Derived Building Blocks

Meninno

2023

Eur J Org Chem

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Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl₃‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates

et al. 2019

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A strategy has been established for the synthesis of 2,4‐diaryl‐1,3‐benzoxazines via a FeCl3‐catalyzed annulation of ortho‐hydroxyphenyl‐substituted para‐quinone methides (p‐QMs) and imidates. This transformation proceeds under mild, operationally‐simple conditions in a very short time. A wide range of substrates was accessed in this facile chemical transformation, in which the cyclized products were isolated in good to excellent yields (37% to 98%). This reaction not only provides an efficient method for the construction of biologically important 2,4‐diaryl‐1,3‐benzoxazines but also greatly enriches the chemistry of p‐QMs.magnified image

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Organocatalytic Remote Asymmetric Inverse‐Electron‐Demand Oxa‐Diels‐Alder Reaction of Allyl Ketones with Isatin‐Derived Unsaturated Keto Esters

Lin

Hou

et al. 2020

Adv Synth Catal

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A remote cascade asymmetric inverse-electron-demand oxa-Diels-Alder reaction of allyl ketones with isatin-derived β,γ-unsaturated α-keto esters has been developed in the presence of a chiral bifunctional squaramide catalyst. Taking advantage of the secondary amide activating group, a series of enantioenriched 3,4'-pyranyl spirooxindole derivatives bearing three contiguous chiral centers were attained in high yields (84 to > 99%) with excellent enantioselectivities (96-99% ee). Moreover, the gram-scale synthesis and the construction of 1-benzazepine scaffold by the product were also demonstrated.

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Dearomative [4+2] Cycloaddition of Oxindole‐Embedded ortho‐Quinone Methides with 2,5‐Dialkylfurans

Cited by 18 publications

References 74 publications

Organocatalytic Upgrading of Biomass Derived Building Blocks

Organocatalytic Upgrading of Biomass Derived Building Blocks

Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl₃‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates

Organocatalytic Remote Asymmetric Inverse‐Electron‐Demand Oxa‐Diels‐Alder Reaction of Allyl Ketones with Isatin‐Derived Unsaturated Keto Esters

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Dearomative [4+2] Cycloaddition of Oxindole‐Embedded ortho‐Quinone Methides with 2,5‐Dialkylfurans

Cited by 18 publications

References 74 publications

Organocatalytic Upgrading of Biomass Derived Building Blocks

Organocatalytic Upgrading of Biomass Derived Building Blocks

Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl3‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates

Organocatalytic Remote Asymmetric Inverse‐Electron‐Demand Oxa‐Diels‐Alder Reaction of Allyl Ketones with Isatin‐Derived Unsaturated Keto Esters

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Synthesis of 2,4‐Diaryl‐1,3‐benzoxazines via FeCl₃‐Catalyzed Annulation of ortho‐Hydroxyphenyl‐Substituted para‐Quinone Methides with Imidates