Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates DOI

Mengting Tan,

Yunping Zheng, Sen Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9203 - 9209

Published: Oct. 21, 2024

Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between o-aminochalcones and γ-bromocrotonates has been developed. A series cis-2,3-disubstituted indolines cyclopropane-fused tetrahydroquinolines were obtained via two pathways with broad substrate scope moderate to excellent yields under transition-metal-free conditions. It noteworthy that could be used as C1 or C2 synthons by modulating base; particular, both nucleophiles electrophiles generate cyclopropanes for first time.

Language: Английский

Phosphine‐Catalyzed Divergent γ,γ‐ and ε,γ‐Umpolung Domino Additions of Bisoxindoles with Allenoates: Construction of Vicinal All‐Carbon Quaternary Stereocenters and Formal Total Synthesis of Dimeric Cyclotryptamine Alkaloids DOI Open Access
Yufei Zhang, Jing Chen, Hui Yao

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 25, 2025

Comprehensive Summary Vicinal all‐carbon quaternary stereocenters are widely present in natural products and bioactive molecules. However, the construction of such motif one step from readily available starting materials remains a significant challenge. Herein, we report phosphine‐catalyzed divergent γ,γ‐ ε,γ‐umpolung domino addition bisoxindoles with allenoates. This method serves as practical tool for concise synthesis series bisoxindole derivatives bearing sterically hindered vicinal under mild reaction conditions. The applicability this novel was demonstrated gram‐scale three known advanced intermediates total syntheses calycanthine, chimonanthine folicanthine.

Language: Английский

Citations

3
Controllable Phosphine-Catalyzed Three-Component Domino Reaction of Activated Alkenes with Morita–Baylis–Hillman (MBH) Carbonates: Divergent Synthesis of Densely Functionalized Cyclopentanes and Diquinanes DOI

Yi Li,

Xianfei Hu,

Boning Li

et al.

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

Published: Dec. 7, 2024

An unexpected phosphine-catalyzed controllable three-component domino reaction involving [1 + 2 2] annulation and 2]/[3 sequential of 2-arylmethylidene cyanoacetates/malononitriles with Morita-Baylis-Hillman (MBH) carbonates has been developed. A broad range densely functionalized cyclopentanes diquinanes bearing five or four consecutive stereogenic centers, including two all-carbon quaternary stereocenters, were smoothly acquired in moderate to excellent yields under mild conditions from readily available materials. Moreover, this divergent transformation enables the simultaneous generation three new C-C bonds one carbocyclic rings only step.

Language: Английский

Citations

4
Pyridine-Catalyzed Chemoselective Four-Component Cascade Reaction of Aromatic Aldehydes, Malononitrile/Cyanoacetates, MBH Carbonates, and Alcohols DOI
Boning Li,

Xianfei Hu,

Hui Yao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7576 - 7583

Published: Sept. 3, 2024

An efficient pyridine-catalyzed chemoselective four-component cascade reaction of aromatic aldehydes, malononitrile/cyanoacetates, Morita-Baylis-Hillman (MBH) carbonates, and alcohols has been established. This one-pot progressed in an unusual with solvent participation via a Knoevenagel condensation/oxa-Michael addition/S

Language: Английский

Citations

3
Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans DOI

Dan Xiong,

Sen Zhang, Zhiyue Li

et al.

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

Published: April 23, 2025

Herein, we developed an efficient nucleophile-controlled regiodivergent domino reaction between enetriones and γ-bromocrotonates. This method allowed for the rapid synthesis of a range 1,3-dienic esters tetrasubstituted pyrans under metal-free conditions. In presence pyridine, SN2 substitution/Michael addition/elimination sequence formed in satisfactory yields with high E-stereoselectivities. Alternatively, addition/cyclization/cyclopropanation/cyclopropane ring-opening process forged good help Et3N. It is interesting to note that site-selective reactions γ-bromocrotonates at α- or γ-position were readily realized by modulating pyridine Furthermore, simple Et3N act as both nucleophiles substitution Lewis bases deprotonation processes.

Language: Английский

Citations

0
Tertiary Amine‐Catalyzed Stereoretentive Multi‐Component Cascade Reaction of Carboxylic Acids: Facile Synthesis of Cyclic Ureas/Urethanes DOI
Yi Hu,

Yifei Cai,

Yanfei Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 29, 2025

Comprehensive Summary Herein, we developed a tertiary amine‐catalyzed stereoretentive multi‐component cascade reaction featuring an amidation/[4 + 1] annulation/decarboxylation/Curtius rearrangement/[2 n ] annulation sequence. This metal‐free and step‐economic method provided broad range of cyclic ureas/urethanes in green solvent under mild conditions without employing explosive toxic reagents. Importantly, this generated isocyanates situ catalytic via decarboxylation/Curtius rearrangement process dioxazolones.

Language: Английский

Citations

0
Catalyst-Controlled Switchable Formal Retro-Büchner reaction for the Divergent Synthesis of Benzo[b]azepines and 1, 3-Conjugated Dienes DOI

Zhaoxue Wang,

Menghui Guo,

Ping Wu

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 169, P. 134378 - 134378

Published: Nov. 13, 2024

Language: Английский

Citations

2
Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates DOI

Mengting Tan,

Yunping Zheng, Sen Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9203 - 9209

Published: Oct. 21, 2024

Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between o-aminochalcones and γ-bromocrotonates has been developed. A series cis-2,3-disubstituted indolines cyclopropane-fused tetrahydroquinolines were obtained via two pathways with broad substrate scope moderate to excellent yields under transition-metal-free conditions. It noteworthy that could be used as C1 or C2 synthons by modulating base; particular, both nucleophiles electrophiles generate cyclopropanes for first time.

Language: Английский

Citations

1