Asymmetric copper-catalyzed alkynylallylic monofluoroalkylations with fluorinated malonates

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(31), P. 4210 - 4213

Published: Jan. 1, 2024

The unprecedented copper-catalyzed asymmetric alkynylallylic monofluoroalkylation reaction is described

Language: Английский

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Recent advances in copper-catalyzed asymmetric propargylic substitution

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100082 - 100082

Published: July 3, 2024

Language: Английский

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Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11646 - 11656

Published: July 22, 2024

Language: Английский

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Insights into Cu(I)-Catalyzed Decarboxylation of Propargylic Cyclic Carbonates with Amines: Origins of Regioselectivity and Enantioselectivity

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

Published: May 21, 2025

Chiral α-functionalized α-amino ketones are sought-after compounds for drug development; however, their acyclic enantioselective synthesis with amines as nucleophiles remains challenging. The catalytic decarboxylation of propargylic cyclic carbonates through metal-allenylidene intermediates has proven to be an efficient route chiral quaternary centers, but its mechanisms require clarification. Herein, we computationally investigate the Cu(I)-catalyzed propargyl aniline [Guo, W. J. Am. Chem. Soc. 2021, 143, 7629-7763]. calculation results elucidate mechanistic details reaction and reveal that enantioselectivity stems from distinct noncovalent interactions in (R)- (S)- transition states, while regioselectivity arises lower steric hindrance attack at C5 versus C1 atom zwitterionic intermediate. IGMH analysis further validates enantiocontrol. theoretical offer insights into nucleophiles, advancing understanding amination aiding development this research field.

Language: Английский

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Asymmetric Remote Leaving Group-Promoted Propargylic Substitution

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 10030 - 10038

Published: May 29, 2025

Language: Английский

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A New Reaction Mode of 3-Halooxindoles: Acting as C–C–O Three-Atom Components for (3+3) Cycloaddition to Access Indolenine-Fused 2H-1,4-Oxathiines

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9191 - 9196

Published: Dec. 19, 2023

Herein, we report an unprecedented implementation of 3-halooxindoles as C-C-O three-atom components for (3+3) cycloaddition with pyridinium 1,4-zwitterionic thiolates, affording structurally diverse indolenine-fused 2H-1,4-oxathiines in moderate to high yields. A combined experimental and computational mechanistic study suggests that the reaction proceeds through addition a S conjugate o-azaxylylene intermediate, followed by O-Michael sequential retro-Michael addition/pyridine extrusion pathway.

Language: Английский

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Chiral phosphoric acid-catalyzed enantioselective synthesis of functionalized pyrrolinones containing a geminal diamine core via an aza-Friedel–Crafts reaction of newly developed pyrrolinone ketimines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1437 - 1443

Published: Jan. 1, 2024

A class of novel pyrrolinone ketimines was synthesized for the first time and applied to asymmetric aza-Friedel–Crafts reaction with phenolic compounds.

Language: Английский

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Doubly Stereoconvergent Propargylic Alkylation of α-Cyanocarbonyls: Enantioselective Construction of Vicinal Stereocenters

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 30, 2024

An asymmetric propargylic alkylation of α-cyanocarbonyls is developed for the first time under cooperative Cu(I) and organocatalysis. With ethynyl benzoxazinanones as electrophile, this decarboxylative doubly stereoconvergent reaction evades alkyne hydroamination to furnish acyclic α-propargylic cyanocarbonyls, bearing vicinal tertiary quaternary stereocenters, with high diastereo- enantioselectivity (up >20:1 dr 99.5:0.5 er).

Language: Английский

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An Organometallic Umpolung Approach for Iron‐Mediated Propargylic C–H Etherification

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract Propargylic ethers serve as useful intermediates for the synthesis of a variety complex targets. However, propargylic substitution prefunctionalized alkyne starting materials remains dominant method propargyl ethers, while direct etherification simple alkynes via C−H functionalization largely underreported. Herein, we report an organometallic umpolung approach iron‐mediated etherification. A telescopic protocol deprotonation followed by mild oxidative coupling with alcohols enabled use or functionalized expedient excellent functional group compatibility, chemoselectivity and regioselectivity.

Language: Английский

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Enantioselective [3 + 2] annulation of tryptanthrin-derived ketimines and 2-naphthols: access to polycyclic indolo[2,1-b]quinazoline derivatives

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2002 - 2007

Published: Jan. 1, 2024

An efficient method has been disclosed for the highly enantioselective synthesis of optically pure heptacyclic dihydronaphthofuran-fused indolo[2,1- b ]quinazoline derivatives.

Language: Английский

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