Palladium-catalyzed enantioselective carbonylation reactions

Science China Chemistry, Journal Year: 2022, Volume and Issue: 65(3), P. 441 - 461

Published: Jan. 5, 2022

Abstract Carbonylation, one of the most powerful approaches to preparation carbonylated compounds, has received significant attention from researchers active in various fields. Indeed, impressive progress been made on this subject over past few decades. Among types carbonylation reactions, asymmetric is a straightforward methodology for constructing chiral compounds. Although rhodium-catalyzed enantioselective hydroformylations have discussed several elegant reviews, general review palladium-catalyzed carbonylations still missing. In review, we summarize and discuss recent achievements reactions. Notably, review’s contents are categorized by reaction type.

Language: Английский

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Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(3)

Published: Nov. 2, 2023

With the rapid development of asymmetric catalysis, demand for enantioselective synthesis complex and diverse molecules with different chiral elements is increasing. Owing to unique features atropisomerism, catalytic atropisomers has attracted a considerable interest from chemical science community. In particular, introducing additional elements, such as carbon centered chirality, heteroatomic planar helical into provides an opportunity incorporate new properties axially compounds, thus expanding potential applications atropisomers. Thus, it important perform transformations synthesize bearing multiple elements. spite challenges in transformations, recent years, chemists have devised powerful strategies under organocatalysis or metal synthesizing wide range enantioenriched Therefore, become emerging field. This review summarizes progress this field indicates challenges, thereby promoting horizon.

Language: Английский

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P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(14), P. 8657 - 8739

Published: July 2, 2024

Chiral phosphorus ligands play a crucial role in asymmetric catalysis for the efficient synthesis of useful optically active compounds. They are largely categorized into two classes: backbone chirality and P-stereogenic ligands. Most reported belong to former class. Privileged ones such as BINAP DuPhos frequently employed wide range catalytic transformations. In contrast, latter class has remained small family many years mainly because their synthetic difficulty. The late 1990s saw emergence novel with superior enantioinduction ability Rh-catalyzed hydrogenation reactions. Since then, numerous have been synthesized used This Review summarizes thus far, including stereochemical electronic properties that afford high excellent enantioselectivities. Examples reactions use this described together applications construction key intermediates natural products therapeutic agents. literature covered dates back 1968 up until December 2023, centering on studies published later years.

Language: Английский

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Recent advances in Pd-catalyzed asymmetric cyclization reactions

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 53(2), P. 883 - 971

Published: Dec. 18, 2023

This review aims to collect advancements in enantioselective palladium-catalyzed cyclization reactions over the past eleven years, and it is organized into thirteen sections depending on different types of transformations involved.

Language: Английский

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Cobalt-Catalyzed Enantioselective Cross-Electrophile Couplings: Stereoselective Syntheses of 5–7-Membered Azacycles

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(30), P. 16464 - 16473

Published: July 21, 2023

Cobalt complexes of chiral pyrox ligands catalyzed enantioselective reductive couplings nonconjugated iododienes with aryl iodides or alkenyl bromides. The reaction enabled stereoselective syntheses 5-7-membered azacycles carrying quaternary stereocenters. Mechanistically, cross-electrophile selectivity originated from selective coupling alkylcobalt(I) generated after cyclization iodides.

Language: Английский

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Enantioselective synthesis of molecules with multiple stereogenic elements

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(22), P. 11165 - 11206

Published: Jan. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Language: Английский

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Recent Developments in Enantioselective Domino Reactions. Part A: Noble Metal Catalysts

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(5), P. 620 - 681

Published: Jan. 17, 2023

Abstract This review updates the field of enantioselective domino reactions promoted by chiral catalysts derived from noble metals, including palladium, silver, rhodium, ruthenium, iridium and gold, published since beginning 2019. It illustrates how much a diversity these allow unprecedented asymmetric many types to be achieved with excellent enantioselectivity, giving direct access wide variety complex molecules. magnified image

Language: Английский

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Atroposelective synthesis of biaxial bridged eight-membered terphenyls via a Co/SPDO-catalyzed aerobic oxidative coupling/desymmetrization of phenols

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 30, 2024

Abstract Bridged chiral biaryls are axially compounds with a medium-sized ring connecting the two arenes. Compared plentiful methods for enantioselective synthesis of biaryl compounds, synthetic approaches this subclass bridged atropisomers limited. Here we show an atroposelective 1,3-diaxial eight-membered terphenyl through Co/SPDO (spirocyclic pyrrolidine oxazoline)-catalyzed aerobic oxidative coupling/desymmetrization reaction prochiral phenols. This catalytic desymmetric process is enabled by combination earth-abundant Co(OAc) 2 and unique SPDO ligand in presence DABCO (1,4-diaza[2.2.2]bicyclooctane). An array diaxial terphenyls embedded azocane can be accessed high yields (up to 99%) excellent enantio- (>99% ee) diastereoselectivities (>20:1 dr).

Language: Английский

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Catalytic asymmetric synthesis of medium-sized bridged biaryls

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(79), P. 11031 - 11044

Published: Jan. 1, 2022

Despite the persistent presence of medium-sized (seven- to nine-membered) scaffolds in natural products and biologically active molecules, their asymmetric syntheses have always been considered a formidable task; therefore, they remained underdeveloped when compared enantioselective synthesis five- six-membered ring scaffolds. One important class such frameworks includes seven- nine-membered biaryl bridged carbo- heterocycles. These medium-ring-sized possess more configurational stability than related smaller structures are common features valuable products, bioactive compounds, chiral catalysts, molecular motors. Due these exciting properties broad applications, over last few years, catalytic biaryls has seen an upsurge. This highlight article describes development organocatalysed transition-metal catalysed transformations for procuring seven-, eight-, bearing axis/one or carbon centres.

Language: Английский

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Stereoselective synthesis of functionalized azepines via gold and palladium relay catalysis

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4685 - 4691

Published: Jan. 1, 2022

We developed a cycloisomerization/asymmetric [4 + 3] cycloaddition cascade reaction via gold/palladium relay catalysis, furnishing enantioenriched furan-fused azepines efficiently.

Language: Английский

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