Chiral P,N,N‐Ligands for Asymmetric Hydrogenation

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2165 - 2185

Published: April 9, 2024

Abstract The chiral P,N,N‐ligands represented a new type of tridentate ligand developed in recent years and displayed wide utilities asymmetric catalysis. In the past decades, numerous with ferrocene, phenethylamine spiro backbones were synthesized by addition an aminopyridine, imidazole or diamines coordinating group. These showed excellent performance ruthenium, iridium, manganese, cobalt‐catalyzed hydrogenations. A range substrates, including simple ketones, α‐halogenated α‐hydroxy α‐ β‐amino keto‐ ones, α‐, γ‐, δ‐keto acids, β‐keto amides, β‐ esters, β‐enones, olefins, imines, quinolines indoles, could be hydrogenated to afford corresponding products high yields enantioselectivities. this review, progress on hydrogenation C=O, C=N, C=C bonds was summarized.

Language: Английский

Highly Efficient and Enantioselective Iridium-Catalyzed Asymmetric Reductive Cycloetherification

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

A catalytic protocol for the iridium-catalyzed asymmetric hydrogenation (AH) of γ- or δ-hydroxy ketones to rapidly assemble various aliphatic enantioenriched tetrahydrofurans (THFs) tetrahydropyrans (THPs) is disclosed. wide range THFs THPs were obtained in high yields and excellent enantioselectivities (up 99% up 96.5:3.5 er). The dynamic kinetic resolution (DKR-AH) process was also achieved, simultaneously constructing THP scaffolds with two contiguous stereogenic centers stereoselectivities 92% yield, 98.5:1.5 er >20:1 dr). Mechanistic investigation indicates that key step reaction involves AH challenging cyclic, oxocarbenium ions. Furthermore, this enantioselective approach could be carried out on a gram scale, cyclic ethers further transformed into an array useful building blocks natural products bioactive molecules.

Language: Английский

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