Enantioselective Synthesis of Hydrindanes via Palladium-Catalyzed Asymmetric Desymmetrization of Cyclohexadiene Derivatives

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

Published: Feb. 5, 2025

We herein disclose a strategy for the asymmetric desymmetrization of cyclohexadiene derivatives via palladium-catalyzed Heck and tandem Heck/Tsuji-Trost allylic alkoxylation reaction. By employing DCE as solvent, we obtained variety chiral hydrindanes containing an all-carbon quaternary carbon center tertiary in good yields with excellent enantioselectivities. With alcohols valuable one stereocenter two centers were constructed high level enantioinduction.

Language: Английский

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Electrochemical Fe-catalyzed deoxygenative alkoxycarbonylation of imidazoheterocycles with carbazates

Synthetic Communications, Journal Year: 2025, Volume and Issue: 55(5), P. 422 - 432

Published: Feb. 2, 2025

Imidazo[1,2-a]pyridine derivatives possess widespread applications in the pharmaceutical industry and bioactive natural products. The diverse functionalization of this skeleton has attracted much attention from chemists. Herein, we reported an electrochemical deoxygenative alkoxycarbonylation imidazoheterocycles by using electrons as traceless oxidant under mild oxidant-free conditions. Notably, our strategy provided a green practical approach for introducing ester group into imidazo[1,2-a]pyridine employing easily available bench-stable carbazates source.

Language: Английский

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Divergent Synthesis of Diaza-oxabicyclo[3.2.1]octanes and Dioxa-azabicyclo[3.2.1]octanes via Cascade Cyclizations

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 13, 2025

Bicyclo[3.2.1]octanes widely exist in natural products and bioactive compounds. However, the efficient construction of these skeletons remains a challenge. Herein, we reported convenient synthesis diaza-oxabicyclo[3.2.1]octanes dioxa-azabicyclo[3.2.1]octanes by intramolecular cascade cyclizations. The reaction was performed under transition metal-free conditions with good functional group tolerance. This work provides divergent approaches to bicyclo[3.2.1]octane frameworks.

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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Palladium-Catalyzed Asymmetric Tandem Carbonylation–Heck Reaction of Cyclopentenes to Access Chiral Bicyclo[3.2.1]octenes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(39), P. 8244 - 8248

Published: Sept. 23, 2024

A palladium-catalyzed asymmetric tandem carbonylation-Heck reaction of cyclopentenes with carbon monoxide (CO) has been disclosed. This desymmetrization procedure afforded a series bicyclo[3.2.1]octenes one chiral quaternary and tertiary center in good yields enantioselectivities. proceeds via an acyl-palladium intermediate, followed by migratory insertion the alkenes.

Language: Английский

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