Asymmetric Synthesis of Multicyclic Spirooxindole Derivatives Bearing Stereogenic Quaternary Carbon Atoms

Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2642 - 2646

Published: April 6, 2023

An organocatalyzed stereoselective domino reaction as a facile approach to multicyclic spirooxindole derivatives bearing two stereogenic quaternary carbon atoms is reported. The alkyl-substituted chiral thiourea catalyst was efficient for the tolerate wide range of substrates, furnishing new class an O,O-acetal-fused tricyclic skeleton or tetrahydroxanthone moiety in moderate good yields with excellent selectivities. products generated from this method have promising anticancer activities.

Language: Английский

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Rapid Construction of Tricyclic Furanobenzodihydropyrans by Asymmetric Tandem Reaction

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(3), P. 1815 - 1827

Published: Jan. 16, 2023

A process based on the organocatalyzed Mannich/cycloketalization/transesterification tandem reaction of 1-(2-hydroxyaryl)-1,3-diketones and β,γ-alkynyl α-imino esters has been developed, delivering a variety tricyclic furanobenzodihydropyrans with excellent results (up to 99% yield, ee, >19:1 dr).

Language: Английский

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Catalytic Asymmetric [3 + 2] Cycloaddition of Exocyclic Enol Ethers for the Synthesis of Spiroketals

Precision Chemistry, Journal Year: 2023, Volume and Issue: 1(7), P. 423 - 428

Published: July 24, 2023

An efficient synthesis of chiral benzannulated spiroketals via catalytic asymmetric [3 + 2] cycloaddition exocyclic enol ethers with p-quinones was achieved. The transformation enabled by a N,N′-dioxides/TmIII complex as the Lewis acid catalyst and afforded series enantiomerically enriched spiroketal derivatives in good yields (up to 99%) enantioselectivities 98% ee). Topographic steric maps distribution buried volumes catalysts Cavallo's SambVca 2 tool were used elucidate enantioinduction raised ligands metal ions.

Language: Английский

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Asymmetric Synthesis of Hydrodibenzofurans from Norcaradienes: Kinetic Resolution via [3 + 2] Cycloaddition with Quinones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3844 - 3849

Published: April 25, 2024

The catalytic asymmetric [3 + 2] cycloaddition of racemic norcaradienes with quinones to construct multicyclic hydrodibenzofurans was achieved by the use chiral N,N′-dioxide/metal complex catalysts. Kinetic resolution accompanied partial racemization occurred, and one enantiomer in prior acted as C2 synthon participate diastereoselective cycloaddition. An enantiodivergent synthesis via a switch metal ions observed when naphthoquinone used partner. DFT calculations revealed profiles processes.

Language: Английский

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Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-b]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14670 - 14675

Published: Oct. 10, 2023

An asymmetric [3+2] cycloaddition of quinone esters with 2,3-dihydrofuran has been realized via a newly developed Cu(II)/SPDO complex. It provides straightforward access to 2,3,3a,8a-tetrahydrofuro[2,3-b]benzofurans (TFB) high enantioselectivity (up 97.5:2.5 er) and diastereoselectivity (all >20:1 dr). The resulting adducts contain two adjacent stereocenters continuously functionalized benzene ring. Additionally, this transformation could be easily performed on gram scale, allowing for expedient synthesis natural dihydroaflatoxin D2 aflatoxin B2.

Language: Английский

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Annulations involving p-benzoquinones: stereoselective synthesis of fused, spiro and bridged molecules

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(18), P. 8243 - 8276

Published: Jan. 1, 2024

The present review summarizes the recent advances (2018–2023) in stereoselective annulation involving p -benzoquinones for construction of fused, spiro and bridged/cage frameworks.

Language: Английский

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Side arm modified chiral bisoxazoline ligands: Recent development and prospect in asymmetric catalysis

Tetrahedron, Journal Year: 2022, Volume and Issue: 129, P. 133121 - 133121

Published: Oct. 31, 2022

Language: Английский

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Strategies and Methods for the Catalytic Asymmetric Synthesis of Benzofuran/Benzopyran Fused Acetals: A Review

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4320 - 4333

Published: Nov. 17, 2023

Benzofuran- and benzopyran-fused polycyclic acetals are found in a variety of biologically active natural products. The synthetic methods toward this class heterocycles have fascinated one the most intensive pursuits total synthesis. Nevertheless, stereoselective towards rapid construction such skeletons still remain challenging for organic chemists. Significant progress has been made research area recent years, however, literature on enantioselective approaches to construct these molecules not fully reviewed. Driven by their intriguing complex scaffolds with potential usefulness, we compose advances review covering all important works field. We hope will promote future area.

Language: Английский

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Transition Metal‐Catalyzed Enantioselective Synthesis of Chiral Five‐ and Six‐Membered Benzo O‐heterocycles

The Chemical Record, Journal Year: 2023, Volume and Issue: 23(11)

Published: July 4, 2023

Enantiomerically enriched five- and six-membered benzo oxygen heterocycles are privileged architectures in functional organic molecules. Over the last several years, many effective methods have been established to access these compounds. However, comprehensive documents cover updated methodologies still highly demand. In this review, recent transition metal catalyzed transformations lead chiral presented. The mechanism chirality transfer or control processes also discussed details.

Language: Английский

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Bifunctional Squaramide‐Catalyzed Asymmetric Michael/Cyclization Reactions of 3‐Hydroxychromenones with Isatylidenemalononitriles

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(20)

Published: May 24, 2024

Abstract A squaramide‐catalyzed asymmetric Michael/cyclization tandem reaction between 3‐hydroxychromenones and isatylidenemalononitriles was developed. Using this strategy, a wide scope of spiro[indoline‐3,4′‐pyrano[3,2‐b]chromene] derivatives, which combined chromone, pyran, indolone in one molecule, could be obtained moderate to excellent yields (up 94 %) with enantioselectivities 95 % ee). In addition, the scaled‐up experiment also confirmed synthetic practicality strategy.

Language: Английский

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