Enantio- and Diastereoselective Synthesis of P-Stereogenic Phospholane Oxides via Cobalt-Catalyzed Hydroalkylation

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

Published: April 10, 2025

Chiral phospholane ligands and catalysts have been widely applied in asymmetric catalysis synthesis. However, the construction of chiral skeleton remains challenging primarily relies on use auxiliaries or resolution. In this work, a highly enantioselective diastereoselective synthesis P-stereogenic oxides has achieved through cobalt-catalyzed desymmetric hydroalkylation strategy. This method enables two discrete stereocenters with excellent yields enantiomeric excesses.

Language: Английский

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Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis

JACS Au, Journal Year: 2024, Volume and Issue: 4(6), P. 2312 - 2322

Published: June 11, 2024

Enantioenriched 3-methylpyrrolidine, with its unique chiral nitrogen-containing core skeleton, exists widely in various functional molecules, including natural products, bioactive compounds, and pharmaceuticals. Traditional methods for synthesizing these valuable methyl-substituted heterocycles often involve enzymatic processes or complex procedures auxiliaries, limiting the substrate scope efficiency. Efficient catalytic methylation, especially an enantioselective manner, has been a long-standing challenge chemical synthesis. Herein, we present novel approach remote stereoselective installation of methyl group onto N-heterocycles, leveraging CoH-catalyzed asymmetric hydromethylation strategy. By effectively combining commercial cobalt precursor modified bisoxazoline (BOX) ligand, variety easily accessible 3-pyrrolines can be converted to enantiopure 3-(isotopic labeling)methylpyrrolidine compounds outstanding enantioselectivity. This efficient protocol streamlines two-step synthesis enantioenriched which previously required up five six steps under harsh conditions expensive starting materials.

Language: Английский

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Cobalt‐Catalyzed Hydroarylation of 2,3‐Dihydrofuran to Access α‐Arylated Tetrahydrofurans

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract The α ‐arylated tetrahydrofurans, commonly found in biologically active molecules, exhibit diverse biological activities and pharmacological effects. functionalization of 2,3‐dihydrofuran offers a potential route for the synthesis substituted tetrahydrofurans. Nevertheless, development earth‐abundant metal‐catalyzed regioselective hydrofunctionalization tetrahydrofurans remains to be pursued. Herein, we report cobalt‐catalyzed hydroarylation 2,3‐dihydrofuran, which serves as first example cobalt hydride‐catalyzed alkene hydroarylation. This reaction provides an efficient method with high efficiency, exclusive ‐arylation selectivity, remarkable functional group compatibility.

Language: Английский

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Multifunctional Photobleaching Visible Radical/Cationic Photoinitiators Based on 5-Membered Aromatic Heterocyclic-Bis-Chalcone-Oxime Esters

ACS Applied Polymer Materials, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 23, 2024

Language: Английский

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