Recent advances in metal-free catalytic enantioselective higher-order cycloadditions

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1824 - 1842

Published: Jan. 1, 2024

In this review, we briefly summarize the recent research progress in enantioselective higher-order cycloadditions, focusing on preparation of medium-sized and multicyclic chiral molecules by metal-free catalysis.

Language: Английский

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Application of Asymmetric Catalysis in Chiral Pesticide Active Molecule Synthesis

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(31), P. 17153 - 17165

Published: July 25, 2024

The different configurations of chiral pesticides generally have significant influence on their biological activities. Chiral agrochemicals with high optical purities become a prominent topic in the research field new due to advantages including lower toxicity, higher efficiency, and reduced residue levels. However, most commercially available that possess elements are still used racemic forms. To date, asymmetric catalysis has emerged as versatile tool for enantioselective synthesis various novel pesticide active molecules. This perspective provides comprehensive overview applications diverse catalytic approaches facile preparation numerous molecules, our own outlook future development this highly direction is also presented at end review.

Language: Английский

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Access to Chiral Bridged Biaryls via Brønsted Acid-Catalyzed Asymmetric Addition of Alcohols to Fluoroalkylated Biaryl Oxazepines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 24, 2025

We disclose herein a chiral phosphoric-acid-catalyzed enantioselective addition reaction of alcohols to fluoroalkylated biaryl 1,3-oxoazepines, which furnished wide range bridged biaryls bearing quaternary carbon stereocenter on the seven-membered ring in high yields (up 99%) with excellent enantioselectivities 98% ee). Our method can be used for modification several natural products and bioactive molecules. Preliminary studies revealed that obtained this exhibit good vitro bioactivities against two plant pathogens.

Language: Английский

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Enantioselective Construction of Spirooxindole‐γ‐butyrolactones via NHC‐Bound Isobenzofulvene [10π+2π] Cycloaddition

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 12, 2025

Comprehensive Summary We report an N ‐heterocyclic carbene (NHC)‐catalyzed [10π+2π] cycloaddition between indene‐2‐carbaldehydes and isatins, delivering spirooxindole‐γ‐butyrolactones with moderate yields (up to 68%) excellent enantioselectivity 93% ee). This transformation proceeds via NHC‐bound isobenzofulvene intermediates represents the first successful application of all‐carbon higherene in NHC‐catalyzed cycloadditions.

Language: Английский

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NHC-Catalyzed Cross-Coupling of Aldehydes for C(sp2)−O Bond Formation

Published: March 7, 2024

In the past few decades, N-heterocyclic carbenes (NHCs) open new field of organocatalysis in synthetic organic chemistry. This review highlights dramatic progress NHC-catalyzed C−O bond formation based on activation aldehyde C(sp2)−H bonds. The oxidative and redox transformations for synthesis various molecules with structural diversity complexity are summarized. Furthermore, methods strategies NHC catalysis emerging continuously; thus, cooperative Brønsted acid, hydrogen-bonding catalyst, transition-metal photocatalyst is also described.

Language: Английский

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NHC-Catalyzed Reaction of Aldehydes for C(sp2)–O Bond Formation

Catalysts, Journal Year: 2024, Volume and Issue: 14(4), P. 219 - 219

Published: March 22, 2024

In the past few decades, N-heterocyclic carbenes (NHCs) have opened new field of organocatalysis in synthetic organic chemistry. This review highlights dramatic progress NHC-catalyzed C–O bond formation based on activation aldehyde C(sp2)–H bonds. The oxidative and redox transformations for synthesis various molecules with structural diversity complexity are summarized. Furthermore, methods strategies NHC catalysis emerging continuously; thus, cooperative Brønsted acid, hydrogen-bonding catalyst, transition-metal photocatalyst also described.

Language: Английский

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Highly Enantioselective Construction of the Polycyclic Piperazin-2-ones via NHC-Catalyzed [12 + 2] Cycloadditions

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7917 - 7922

Published: Oct. 24, 2023

NHC-catalyzed diastereoselective and enantioselective [12 + 2] higher-order cycloadditions of 5H-benzo[a]-pyrrolizine-3-carbaldehydes with cyclic sulfonic imines are described. Various optically pure polycyclic piperazin-2-ones were successfully constructed under mild reaction conditions excellent diastereoselectivities enantioselectivities. The generated chiral could be transformed to planar-chiral nine-membered amides via squaramide-catalyzed asymmetric ring-expansion reactions.

Language: Английский

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Five-membered ring systems: With more than 1 N atom

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 211 - 257

Published: Jan. 1, 2024

Language: Английский

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