Asymmetric 1,4-Reduction of Pyrano[2,3-b]indoles with Hantzsch Ester by Chiral Phosphoric Acid DOI

Junyan Zhao,

Man Wang,

Ran Song

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7520 - 7524

Published: Sept. 4, 2024

A highly regioselective and enantioselective transfer hydrogenation of pyrano[2,3-

Language: Английский

Asymmetric cascades of the π-allyl complex: a journey from transition-metal catalysis to metallaphotocatalysis DOI
Santosh K. Nanda

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(76), P. 11298 - 11319

Published: Jan. 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.

Language: Английский

Citations

10
Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings DOI
Jan Otevřel, Macarena Eugui,

Sebastijan Ričko

et al.

Nature Synthesis, Journal Year: 2023, Volume and Issue: 2(12), P. 1142 - 1158

Published: Nov. 13, 2023

Language: Английский

Citations

10
Enantioselective and Regiodivergent Synthesis of Dihydro-1,2-oxazines from Triene-Carbamates via Chiral Phosphoric Acid-Catalysis DOI

Emma Naulin,

Marine Lombard,

Vincent Gandon

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(48), P. 26504 - 26515

Published: Nov. 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.

Language: Английский

Citations

10
Asymmetric Catalytic Transformations of Aza‐ortho‐ and Aza‐para‐Quinone Methides DOI Creative Commons
Mercedes Zurro, Aitor Maestro

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(13)

Published: May 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.

Language: Английский

Citations

7
Recent progress in asymmetric rearrangement reactions mediated by chiral Brønsted acids DOI

Xi-Liang Liu,

Mei-Ling Gong,

Xiaodi Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4934 - 4953

Published: Jan. 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

Language: Английский

Citations

2
An unprecedented synthesis of axially chiral biaryls by rearrangement and aromatization of carbocations with central-to-axial conversion of chirality DOI
Qi Liu, Xuedong Li, Liang Cheng

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(9), P. 2998 - 3003

Published: July 2, 2024

Language: Английский

Citations

2
Synergistic Dual Photoredox and Chiral Hydrogen Bonding Catalysis: Recent Advances DOI
Sermadurai Selvakumar

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(10)

Published: Aug. 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.

Language: Английский

Citations

6
Enantioselective synthesis of pyrroloquinolines via a three-component Povarov reaction with aminoindoles DOI

Zijie Zhou,

Ling Ye, Yang Lu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6219 - 6224

Published: Jan. 1, 2023

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

Language: Английский

Citations

4
Multiple Isocyanide insertions promoted by protic and Lewis acids DOI Creative Commons

John Kornfeind,

Fraser F. Fleming

Tetrahedron Chem, Journal Year: 2023, Volume and Issue: 9, P. 100056 - 100056

Published: Dec. 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

Language: Английский

Citations

4
Michael reaction in organocascade catalysis: A powerful tool for creating architectural complexity in the construction of medicinally privileged heterocyclic scaffolds DOI
Ram Naresh Yadav, Md. Firoj Hossain, Devalina Ray

et al.

Catalysis Reviews, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 266

Published: April 24, 2024

Language: Английский

Citations

1