Asymmetric cascades of the π-allyl complex: a journey from transition-metal catalysis to metallaphotocatalysis

Chemical Communications, Год журнала: 2023, Номер 59(76), С. 11298 - 11319

Опубликована: Янв. 1, 2023

The enantioselective catalytic cascade involving Tsuji-Trost allylation has provided a viable strategy for the construction of multiple asymmetric C-C and C-X centres numerous methods have been developed around it synthesis various vital scaffolds. synthetic utility this was enhanced by replacing customary allyl acetates with ethylene diacetates/dicarbonates, vinyl epoxides, oxetanes, carbonates, cyclopropanes, enynes, dienes using transition-metal catalysis. One more milestone achieved when metallaphotocatalysis necessary platform these cascades cheaper metal. This review will provide summary from 2015.

Язык: Английский

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Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings

Nature Synthesis, Год журнала: 2023, Номер 2(12), С. 1142 - 1158

Опубликована: Ноя. 13, 2023

Язык: Английский

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Enantioselective and Regiodivergent Synthesis of Dihydro-1,2-oxazines from Triene-Carbamates via Chiral Phosphoric Acid-Catalysis

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(48), С. 26504 - 26515

Опубликована: Ноя. 27, 2023

Conjugated trienes are fascinating building blocks for the rapid construction of complex polycyclic compounds. However, limited success has been achieved due to challenging regioselectivity control. Herein, we report an enantio- and diastereoselective process allowing regioselectively control functionalization NH-triene-carbamates. Synthesis chiral cis-3,6-dihydro-2H-1,2-oxazines is by a phosphoric acid catalyzed Nitroso-Diels-Alder cycloaddition involving [(1E,3E,5E)-hexa-1,3,5-trien-1-yl]carbamates. Moreover, modular access three different regioisomers with excellent diastereoselectivities high enantioselectivities obtained careful choice reaction conditions. A computational study reveals that influenced steric demand substituents at 6-position triene, as well noncovalent interactions between two partners. Utility each regioisomeric cycloadduct highlighted variety synthetic transformations.

Язык: Английский

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Asymmetric Catalytic Transformations of Aza‐ortho‐ and Aza‐para‐Quinone Methides

ChemCatChem, Год журнала: 2023, Номер 15(13)

Опубликована: Май 3, 2023

Abstract The catalytic methodologies for the derivatization of aza‐QM have recently appeared in literature and involve organocatalytic organometallic approaches. This review aims at analyzing diverse systems involving chiral NHC carbenes, phosphoric acids, phosphoramidites, phosphine copper palladium catalysis showing its applicability synthesis a away N ‐containing compounds which many cases biological activity.

Язык: Английский

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Recent progress in asymmetric rearrangement reactions mediated by chiral Brønsted acids

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4934 - 4953

Опубликована: Янв. 1, 2024

This review presents an overview of recent developments and trends in chiral Brønsted acid mediated rearrangement reactions. Different mechanisms activation modes are summarized to illustrate the regio- stereo-selectivity

Язык: Английский

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An unprecedented synthesis of axially chiral biaryls by rearrangement and aromatization of carbocations with central-to-axial conversion of chirality

Science China Chemistry, Год журнала: 2024, Номер 67(9), С. 2998 - 3003

Опубликована: Июль 2, 2024

Язык: Английский

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Synergistic Dual Photoredox and Chiral Hydrogen Bonding Catalysis: Recent Advances

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(10)

Опубликована: Авг. 23, 2023

Abstract In the last two decades, chiral hydrogen bonding catalysis has been enormously utilized to trigger several valuable synthetic transformations. Similarly, modern day radical chemistry witnessed potency of visible light photoredox generate radicals via single electron transfer pathway. Recently, their cooperative effect proved be a key strategy access many elegant transformations that are only feasible under synergistic action these catalytic systems. This dual system demonstrates high efficiency for introducing molecular complexity in an enantioselective fashion. this mini review, we have compiled most recent development surfaced three years with particular attention paid mechanistic details and its substrate scope. We hope review will provide readers brief overview advancement application catalysts bond donors reactions.

Язык: Английский

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Enantioselective synthesis of pyrroloquinolines via a three-component Povarov reaction with aminoindoles

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(24), С. 6219 - 6224

Опубликована: Янв. 1, 2023

This protocol provides concise access to enantioenriched pyrroloquinolines, and presents an alternative methodology for functionalizing the carbocyclic ring of indoles.

Язык: Английский

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Multiple Isocyanide insertions promoted by protic and Lewis acids

Tetrahedron Chem, Год журнала: 2023, Номер 9, С. 100056 - 100056

Опубликована: Дек. 9, 2023

Complexation of Lewis acids to electrophiles triggers the sequential insertion two or more isocyanides resulting in valuable iminonitriles heterocycles. The number insertions is controlled by nature alkyl- arylisocyanide and presence a proximal nucleophile capable attacking intermediate nitrilium; loss an alkyl group from nitrilium attack terminates further isocyanide insertions. mechanistic survey protic acid-promoted aims provide fundamental understanding reactivity selectivity facilitate synthetic applications. review structured with introductory overview followed analysis before moving double insertions, which are most prevalent, then triple insertions; concludes sole example quadruple insertion. hope that insight contained will aid applying acid-activated prepare array complex

Язык: Английский

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Michael reaction in organocascade catalysis: A powerful tool for creating architectural complexity in the construction of medicinally privileged heterocyclic scaffolds

Catalysis Reviews, Год журнала: 2024, Номер unknown, С. 1 - 266

Опубликована: Апрель 24, 2024

Язык: Английский

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