Acid–base-sensitive allylic oxidation of 2-allylbenzoic acids to form phthalides

Chuc, Le Thi Ngoc; Nguyen, Thi Anh Hong; Hou, Duen Ren

doi:10.1039/d0ob00303d

Cited by 10 publications

(4 citation statements)

References 80 publications

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“…In 2020, Hou et al reported an allylic oxidation of 2allylbenzoic acids in presence of White catalyst (Scheme 17). [22] Nine examples of 3-ethylidenephthalides were obtained with average to good yields as a mixture of Z and E stereoisomers.…”

Section: Miscellaneous Cyclizationsmentioning

confidence: 99%

Preparation of 3‐Alkylidenephthalides: Recent Advances

et al. 2022

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3-Alkylidenephthalides represent an important class of natural compounds which are also valuable synthetic precursors for the preparation of phthalides. While recent reviews reported the great interest of the phthalides in the field of medicinal chemistry, few reports are mentioning the recent progress for the synthesis of their unsaturated homologous in the position 3. So, the aim of this report is to present the latest progresses (since 2010 and until 2021) in the synthesis of 3-alkylidenephtalides.www.eurjoc.org

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Section: Miscellaneous Cyclizationsmentioning

confidence: 99%

Preparation of 3‐Alkylidenephthalides: Recent Advances

et al. 2022

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“…The enantioselective synthesis of 3-vinyl phthalides and butenolides is of interest due to their potential as synthons [13] towards an array of bioactive compounds. [4] To initiate the study, we selected 1 a for catalyst screening (Scheme 2). Initial trials focused on the use of Au-and Pd-complexes with P,P-, N,N-, and P,N-ligands and AgOTf as a halide scavenger.…”

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confidence: 99%

Enantioselective Lactonization by π‐Acid‐Catalyzed Allylic Substitution: A Complement to π‐Allylmetal Chemistry

2021

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Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via p-acid catalysis. More specifically, a catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel Pd II -catalyst containing the imidazole-based P,N-ligand (S)-StackPhos is reported. The high-yielding reactions are operationally simple to perform with enantioselectivities up to 99 % ee. This strategy facilitates the replacement of a poor leaving group with what would ostensibly be a better leaving group in the product avoiding complications arising from racemization by equilibration.

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confidence: 99%

“…Considering that esters and lactones are ubiquitous in biologically active compounds, [4] preparation by AAA would also be extremely useful, but this is problematic because they are easily ionized under the conditions and are therefore prone to racemization. [5] Trost notes that the problem is "more severe than it appears at first glance" [5a] and con-sequently ester-forming Pd-AAA is scarce.…”

mentioning

confidence: 99%

Enantioselective Lactonization by π‐Acid‐Catalyzed Allylic Substitution: A Complement to π‐Allylmetal Chemistry

2021

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Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non‐racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π‐acid catalysis. More specifically, a catalytic enantioselective dehydrative lactonization of allylic alcohols using a novel PdII‐catalyst containing the imidazole‐based P,N‐ligand (S)‐StackPhos is reported. The high‐yielding reactions are operationally simple to perform with enantioselectivities up to 99 % ee. This strategy facilitates the replacement of a poor leaving group with what would ostensibly be a better leaving group in the product avoiding complications arising from racemization by equilibration.

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Acid–base-sensitive allylic oxidation of 2-allylbenzoic acids to form phthalides

Abstract: Allylic oxidation of 2-allylbenzoic acids to phthalides, instead of Wacker-type isocoumarins, was achieved with 1,2-bis(phenylsulfinyl)ethane palladium(ii) acetate (White catalyst) and oxygen in DMSO.

Cited by 10 publications

References 80 publications

Preparation of 3‐Alkylidenephthalides: Recent Advances

Preparation of 3‐Alkylidenephthalides: Recent Advances

Enantioselective Lactonization by π‐Acid‐Catalyzed Allylic Substitution: A Complement to π‐Allylmetal Chemistry

Enantioselective Lactonization by π‐Acid‐Catalyzed Allylic Substitution: A Complement to π‐Allylmetal Chemistry

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