Recent Progress in Chiral Quaternary Ammonium Salt-Promoted Asymmetric Nucleophilic Additions

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 1973 - 2001

Published: Jan. 20, 2025

Chiral quaternary ammonium ion-pair organocatalysis has been widely used in the facile synthesis of chiral molecules with challenging stereocenters. Especially, numerous asymmetric nucleophilic addition reactions have facilitated this strategy. This review systematically summarizes additions promoted by salts past decade. The content is organized according to types electrophiles involved these catalytic transformations. Our own perspectives on future development within highly active research field are also provided.

Language: Английский

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Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightfor-ward Access to the (thio)Hydantoin Scaffold

Published: April 26, 2024

A palladium-catalyzed (3+2) cycloaddition between 5-vinyloxazolidine-2,4-diones (VOxD) and (thio)isocyanates is described. Under optimized conditions, an array of (thio)hydantoins was readily prepared enantioselective version this transformation then studied. To illustrate the importance method, a concise synthesis two bioactive compounds, nirvanol mephenytoin, carried out. This work emphasizes synthetic potential VOxD as useful precursors zwitterionic aza-π- allylpalladium II intermediates.

Language: Английский

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New Synthetic Approaches for the Construction of Enantioenriched Molecules Bearing Quaternary Stereocenters

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4294 - 4322

Published: Aug. 17, 2024

Abstract Optically active molecule architectures stand as an important class of organic compounds and occupy a key role in academic industrial communities. Particularly, the molecules bearing quaternary carbon are vital importance because its favorable conformation valuable three‐dimensional molecules, which frequently play broad spectrum functional materials, pharmaceutical relevant natural agrochemicals. Over past few decades, large number synthetic strategies for enantioselective construction with chiral centers have been focus research initiatives. In this review, state‐of‐the‐art toward synthesis enantioenriched stereocenters summarized, could be segmented into four categories: 1) Construction optically by addition to prochiral sp 2 carbon; 2) all‐carbon via substitution at non‐chiral tetra‐substituted 3) kinetic resolution; 4) desymmetrization reactions.

Language: Английский

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Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightforward Access to the (Thio)hydantoin Scaffold

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12370 - 12377

Published: Aug. 24, 2024

A palladium-catalyzed (3 + 2) cycloaddition between 5-vinyloxazolidine-2,4-diones (VOxD) and (thio)isocyanates is described. Under optimized conditions, an array of (thio)hydantoins was readily prepared, enantioselective version this transformation then studied. To illustrate the importance method, a concise synthesis two bioactive compounds, nirvanol mephenytoin, carried out. This work emphasizes synthetic potential VOxD as useful precursors zwitterionic aza-π-allylpalladiumII intermediates.

Language: Английский

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