Carbene‐Catalyzed Asymmetric Ring‐Opening Reaction of Biaryl Lactams to Access Axially Chiral Biaryls^†

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1734 - 1740

Published: March 30, 2024

Comprehensive Summary Axially chiral biaryls represent the most important class of atropisomers, and they widely exist in natural products biologically active molecules. They also constitute a unique scaffold for ligands catalysts organic synthesis. The development synthetic methods to obtain such compounds has received widespread attention, among which catalytically atroposelective ring‐opening configurationally labile represents one attractive strategies. Various substrates with strained cyclic structures, as renowned Bringmann's lactones, can undergo asymmetric transformation into stable atropisomers. Known advancement primarily relies on metal catalyst combined well‐designed ligands, approaches utilizing organocatalysis critical resolution strategy are notably scarce. In this study, we disclosed N ‐heterocyclic carbene (NHC)‐catalyzed reaction biaryl lactams via direct nucleophilic activation. optimized bulky ensures that proceed under mild conditions, affording desired product good excellent yields atroposelectivity.

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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Diastereo- and Enantioselective Catalytic Kinetic Resolution of 2-Substituted 3-Nitro-2H-chromenes

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

Published: March 19, 2025

An unprecedented catalytic kinetic resolution of 2-substituted 3-nitro-2H-chromenes via Rh-catalyzed asymmetric hydrogenation has been developed to simultaneously produce a variety syn-chiral 3-nitro-2H-chromanes containing vicinal stereogenic centers with excellent diastero- and enantioselectivities [diastereomeric ratio (dr) >99:1 up 99.9% enantiomeric excess (ee)] recovered chiral 90–99.9% ee in high yields, respectively, achieving selectivity factors 1057. Moreover, addition 3-nitro-2H-chromanes, this new approach provides concise, atom-economical, straightforward access anti-chiral mammalian target rapamycin (mTOR) inhibitor, (R)-DHM25.

Language: Английский

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N-Heterocyclic Carbene-Catalyzed Chemo- and Enantioselective Three-Component Esterification/Amidation Relay for Access to Planar Chiral Ferrocene Derivatives

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6130 - 6140

Published: April 1, 2025

Language: Английский

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Enantio-, atrop-, and diastereoselective macrolactonization to access type III cyclophanes

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 3, 2025

Language: Английский

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