Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters DOI Creative Commons
Adrián Laviós, Amparo Sanz‐Marco, Carlos Vila

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(11), P. 2149 - 2154

Published: March 16, 2022

The diastereo- and enantioselective dearomative formal [3 + 2] cycloaddition of 2-nitrobenzofurans α-aryl-α-isocyanoacetate esters provides tricyclic compounds bearing the 3

Language: Английский

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

Hélène Pellissier

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

Citations

22

Palladium-Catalyzed Ligand-Directed Divergent Decarboxylative Cycloadditions of Vinyloxazolidine-2,4-diones with 1,3,5-Triazinanes DOI
Zhen‐Hua Wang, Xiaohui Fu, Qun Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1589 - 1594

Published: Feb. 22, 2024

This study demonstrates a highly efficient regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence diphosphine ligand, proceeds via (5+2) pathway to afford 1,3-diazepin-4-ones in excellent yields, while using monophosphine smoothly (3+2) give imidazolidin-4-ones good yields.

Language: Английский

Citations

9

Palladium-Catalyzed Asymmetric Decarboxylation of 5-Vinyloxazolidine-2,4-Diones Triggering the Dearomatization of Electron-Deficient Indoles for the Synthesis of Chiral Highly Functionalized Pyrroloindolines DOI

Pei‐Hao Dou,

Xiaohui Fu, Yan Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3310 - 3315

Published: April 8, 2024

A catalyst system consisting of a chiral phosphoramidite ligand and Pd2(dba)3·CHCl3 causes the decarboxylation 5-vinyloxazolidine-2,4-diones to generate amide-containing aza-π-allylpalladium 1,3-dipole intermediates, which are capable triggering dearomatization 3-nitroindoles for diastereo- enantioselective [3+2] cycloaddition, leading formation series highly functionalized pyrroloindolines containing three contiguous stereogenic centers with excellent results (up 99% yield, 88:12 dr, 96% ee).

Language: Английский

Citations

8

Synthesis of Chiral Heterocycles Through Enantioselective Silver‐Catalyzed Transformations DOI Open Access

Hélène Pellissier

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Abstract This review collects the recent developments in synthesis of chiral heterocycles through enantioselective silver‐catalyzed transformations published since 2018. It demonstrates power silver catalysts as special mild Lewis acids to provide an impressive diversity reaction pathways, such 1,3‐dipolar cycloadditions, various types cyclizations, along with a wide variety more complex domino/tandem reactions, allowing many novel heterocyclic products be achieved high enantioselectivities.

Language: Английский

Citations

1

Dearomative (3 + 2) Cycloadditions of 3-Nitroheteroarenes with Allenyl Sulfones Mediated by Ion Pair Organocatalysis DOI

Léo Birbaum,

Moussa Ndiaye,

Mahmoud Hachem

et al.

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

Published: Feb. 8, 2025

We report the first example of dearomative (3 + 2) cycloadditions 3-nitro(aza)-indole, -benzofuran, and -benzothiophene derivatives in presence allenyl sulfones, using sulfinate ammonium ion pairs as organocatalytic promoters. The methodology provides a new, facile, efficient protocol for synthesis functionalized 2,3-fused cyclopentannulated indolines dihydrobenzofurans.

Language: Английский

Citations

1

Catalytic Enantioselective α-Allylation of Deconjugated Butenolides with Aza-π-allylpalladium 1,4-Dipoles: Access to Optically Pure 2-Piperidones Bearing an All-Carbon Quaternary Stereocenter DOI

Shu‐Pei Yuan,

Qing Bao,

Ting-Jia Sun

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(45), P. 8348 - 8353

Published: Nov. 10, 2022

A palladium-catalyzed enantioselective α-allylation of deconjugated butenolides with aza-π-allylpalladium 1,4-diploes, in situ generated from palladium-mediated decarboxylation cyclic carbamates and amide-substituted acyclic carbonates, has been successfully developed. An array enantioenriched 2-piperidones bearing an all-carbon quaternary stereocenter were obtained high yields excellent enantioselectivities (up to 99% yield ee). The utility this method was also showcased by a large-scale reaction synthetic transformations the product.

Language: Английский

Citations

29

Dearomatization of 3-Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4 + 2] Cycloaddition of 2-Alkylidenetrimethylene Carbonates DOI

Pei‐Hao Dou,

Shu‐Pei Yuan,

Yan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(9), P. 6025 - 6037

Published: April 18, 2022

A dearomatization process of 3-nitroindoles enabled using palladium-catalyzed decarboxylative [4 + 2] cycloaddition either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl has been developed, affording a wide range indoline-fused tetrahydropyrans in good yields with excellent diastereoselectivities. This reaction features substrate scope and mild conditions represents the first example application π-allyl palladium 1,4-[O,C]-dipole species for dearomative electron-deficient heteroarenes.

Language: Английский

Citations

27

Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements DOI
P. Devi, Mohan Neetha, Gopinathan Anilkumar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(21), P. 4332 - 4357

Published: Jan. 1, 2023

Silver catalysis offers environmentally friendly and simple protocols to construct N-heterocycles. Inspired by its appeal, herein we have summarized developments in the silver-catalyzed synthesis of N-heterocycles since 2019.

Language: Английский

Citations

12

Organocatalyzed asymmetric dearomative 1,3‐dipolar cycloaddition of 2‐nitrobenzofurans and N‐2,2,2‐trifluoroethylisatin ketimines DOI
Xiaojian Zhou, Jian‐Qiang Zhao,

Yue‐Qin Lai

et al.

Chirality, Journal Year: 2022, Volume and Issue: 34(7), P. 1019 - 1034

Published: May 6, 2022

Abstract A readily available chiral cyclohexanediamine‐derived bifunctional tertiary amine‐squaramide catalyst is more effective for the asymmetric dearomative 1,3‐dipolar cycloaddition of 2‐nitrobenzofurans and N ‐2,2,2‐trifluoroethylisatin ketimines. range structurally diverse spiro‐fused polyheterocyclic compounds containing oxindole, pyrrolidine, hydrobenzofuran motifs were smoothly obtained in excellent results (up to 99% yield, >20:1 dr all cases up ee). This method features high efficiency, mild reaction conditions, exquisite induction, wide functional group tolerance, great potential scale‐up synthesis, attractive product diversification.

Language: Английский

Citations

17

Thiol-Triggered Tandem Dearomative Michael Addition/Intramolecular Henry Reaction of 2-Nitrobenzofurans: Access to Sulfur-Containing Polyheterocyclic Compounds DOI

Jun-Rui Zhuo,

Jian‐Qiang Zhao, Lei Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2623 - 2628

Published: March 24, 2024

An efficient dearomative cyclization of 2-nitrobenzofurans via a thiol-triggered tandem Michael addition/intramolecular Henry reaction has been developed. A range thiochromeno[3,2-b]benzofuran-11-ols and tetrahydrothieno[3,2-b]benzofuran-3-ols could be obtained in up to 99% yield >20:1 dr. The valuable thiochromone fused benzofurans prepared with the 2-mercaptobenzaldehyde reaction/rearomatization/oxidative dehydrogenation process one-pot two-step operation. mechanism for was tentatively proposed.

Language: Английский

Citations

4