Catalytic Asymmetric Diastereodivergent Synthesis of 2-Alkenylindoles Bearing both Axial and Central Chirality

Precision Chemistry, Год журнала: 2024, Номер 2(5), С. 208 - 220

Опубликована: Апрель 23, 2024

The catalytic asymmetric diastereodivergent synthesis of axially chiral 2-alkenylindoles was established via phosphoric acid-catalyzed addition reactions C3-unsubstituted with

Язык: Английский

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Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8‐Addition of Propargylic Aza‐p‐Quinone Methides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(5), С. 1078 - 1083

Опубликована: Янв. 17, 2024

Abstract An organocatalytic remote stereocontrolled 1,8‐conjugated addition of in situ formed propargylic aza‐ p ‐QMs from α‐(4‐aminophenyl) alcohols and indole‐2‐carboxylates was developed, affording axially chiral tetrasubstituted allenes 62–99% yield with 52–99% ee. The synthetic strategy not only enriches the chemistry ‐quinone methides, but also provides an alternative tool for preparation allenes.

Язык: Английский

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DBU‐Promoted [3 + 2] Cyclization/Retro‐Mannich Cascade Reaction of N‐Aminoisoquinolinium and N‐Aminoquinolinium Derivatives with para‐Quinone Methides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(9), С. 2003 - 2007

Опубликована: Март 12, 2024

Abstract A DBU‐promoted [3+2] cyclization/retro‐Mannich cascade reaction of N ‐aminoisoquinolinium and ‐aminoquinolinium derivatives with para ‐quinone methides has been established, employing a C=C double bond cleavage. broad range salts, are well tolerated, providing the corresponding rearrangement products. Moreover, scaled‐up reactions diverse derivatizations products were also investigated discussed.

Язык: Английский

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Diastereo- and Enantioselective Synthesis of Eight-Membered N-Heterocycles from Benzofuran-Derived Azadienes and Ynones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(2), С. 975 - 985

Опубликована: Янв. 5, 2024

Enantioselective synthesis of eight-membered N-heterocycles represents a long-standing challenge in organic synthesis. Here, by combining the squaramide and DBU catalysis, sequential asymmetric conjugate addition/cyclization reaction between benzofuran-derived azadienes ynones has been well-developed, providing straightforward access to chiral high yields with stereoselectivities. This protocol features use bifunctional catalyst for controlling enantioselectivity products, while is utilized achieve intramolecular cyclization improve diastereoselectivity products.

Язык: Английский

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Catalytic asymmetric formal (2 + 3) cycloaddition involving methyl-substituted 2-indolylmethanols

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4812 - 4819

Опубликована: Янв. 1, 2024

A catalytic asymmetric formal (2 + 3) cycloaddition of methyl-substituted 2-indolylmethanols was established, which delivered various chiral pyrroloindoles in overall high yields with excellent diastereoselectivities and good enantioselectivities.

Язык: Английский

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Organocatalytic Diastereoselective Dearomative [4+2] Cyclodimerization of In‐situ Generated ortho‐Quinone Methides

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(11)

Опубликована: Сен. 12, 2023

Abstract We disclose a catalytic, diastereoselective dearomative [4+2] cyclodimerization of in‐situ generated naphthol‐derived ortho ‐quinone methides for the synthesis spiro‐naphthalenones (having an all‐carbon quaternary stereocenter). This methodology offers wide range spiro‐naphthalenone compounds in high yield with excellent diastereoselectivity and regiospecificity. Moreover, process, diastereomeric interconversion cyclo‐adduct presence NaBH 4 was also observed.

Язык: Английский

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Base-Promoted Chemodivergent Construction of 2H-Chromen-2-one and Chromeno[2,3-c]pyrrole Scaffolds from para-Quinone Methides and α-Alkylidene Succinimides

Organic Letters, Год журнала: 2024, Номер 26(42), С. 9114 - 9119

Опубликована: Окт. 11, 2024

Herein, we evolve a base-promoted synthesis of 2

Язык: Английский

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Copper‐Catalyzed α,β‐Regioselective (2+4) Cycloaddition of Propargylic Esters

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(46)

Опубликована: Сен. 26, 2023

Abstract A copper‐catalyzed α,β‐regioselective (2+4) cycloaddition of propargylic esters with o ‐hydroxyphenyl substituted secondary phosphine oxides (SPOs) was established, which afforded a series phosphorus‐containing six‐membered heterocycles in high yields. This reaction represents the first (2+n) via intermediates copper‐allenylidenes, will enrich chemistry and copper‐allenylidenes. Moreover, this work also application SPOs as 1,4‐dinucleophiles cycloadditions, provides useful protocol for synthesis potential bioactivity.

Язык: Английский

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One-pot synthesis of thioethers from indoles and p-quinone methides using thiourea as a sulfur source

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(41), С. 8289 - 8293

Опубликована: Янв. 1, 2023

Thiourea is an inexpensive and user friendly sulfur reagent that acts as a source. A simple efficient protocol has been developed to access thioethers by reacting indoles with p-quinone methides using thiourea the In our experiments, reaction apparently proceeded through S-(3-indolyl)isothiuronium iodide intermediate subsequent generation of indolethiol attacked 1,6 position give desired in good excellent yields.

Язык: Английский

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Organo‐Catalyzed Intermolecular Dehydrative Coupling Reaction to Prepare Arylacetic Acid Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 366(3), С. 502 - 507

Опубликована: Дек. 23, 2023

Abstract Herein, the use of triphenylmethylium tetrakis(pentafluorophenyl)borate as an efficient catalyst for intermolecular dehydrative coupling p ‐hydroxymandelic acid hydrate with substituted aromatic amines and (thio)phenols was developed, which allows preparation arylacetic derivatives in a convenient manner. Notably, this method offers several advantages, including being prefunctionalization free, high atom efficiency, regioselectivity. Additionally, it exhibits broad substrate scope, enabling synthesis range derivatives. Furthermore, can also be applied to etherification arylthiol derivatives, facilitating various thiolated products, would enhance applicability potential utility organic synthesis.

Язык: Английский

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