DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes DOI

Dongqiu Li,

Jiale Wu, Lulu Yang

et al.

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

Published: Dec. 20, 2024

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, use the β- ε-carbons for bond formation, presenting new regiodivergent C4 synthons Lewis base-catalyzed annulations.

Language: Английский

Phosphine-Catalyzed Domino Annulation of γ-Vinyl Allenoates: Synthesis of Tetrahydrofuro[3,2-c]quinoline Derivatives DOI
Mengmeng Ma,

Jiaxu Feng,

Wei Cai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(19), P. 4037 - 4042

Published: May 8, 2024

A novel phosphine-catalyzed domino annulation reaction of γ-vinyl allenoates and o-aminotrifluoacetophenones for the construction terahydrofuro[3,2-c]quinoline derivatives has been developed. In this reaction, two kinds compounds containing CF3 groups were obtained with good yields under mild conditions, three new C–N, C–C, C–O bonds can be built in one step, selectivity is achieved by adjusting conditions. Furthermore, preliminary studies on an asymmetric variant proceeded moderate enantioselectivity.

Language: Английский

Citations

5
Construction of C–P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical–Radical Coupling DOI
Lulu Yang, Jiale Wu, Yang Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3208 - 3212

Published: April 10, 2024

Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R2PCl), which forms fragile C═N–O–PR2 species that undergoes N–O homolysis, fragmentation, and radical–radical coupling, leading to the formation cyano-containing phosphine oxides in good yields. The features an situ activation for radical generation, R2PCl plays dual role as both activator reactant.

Language: Английский

Citations

4
Phosphine-catalyzed reaction of cyclopropenones with water: divergent synthesis of highly functionalized γ-butenolides, trisubstituted α,β-unsaturated acids and anhydride DOI
Fujuan Li, Dan Yang,

Hongyan Qu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A catalyst-regulated phosphine-catalyzed reaction involving cyclopropenones and water has been realized, which can be utilized for the preparation of γ-butenolides trisubstituted α,β-unsaturated acids.

Language: Английский

Citations

0
Enantioselective Synthesis of Cyclopentenes by (3+2) Annulation via a 2‐Carbon Phosphonium DOI Creative Commons
Antonia Seitz, Jeremy T. Maddigan‐Wyatt, Jing Cao

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(35)

Published: May 15, 2024

Abstract Herein we report a catalytic enantioselective (3+2) annulation, in which vinyl phosphonium intermediate serves as the 2‐carbon component. The reaction involves an α‐umpolung β‐umpolung coupling sequence, enabled by β‐haloacrylates and chiral enantioenriched phosphepine catalysts. shows good generality, providing access to array of cyclopentenes, with mechanistic studies supporting stereospecific formation which, then undergoes annulation turn over limiting catalyst elimination. Beyond defining new approach these demonstrate that can replace ynoates designs require exclusive umpolung at α‐ β‐positions.

Language: Английский

Citations

1
Enantioselective Synthesis of Cyclopentanes by Phosphine-Catalyzed β,γ-Annulation of Allenoates DOI

Chenxi Zhang,

Jeremy T. Maddigan‐Wyatt,

Xuan B. Nguyen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7800 - 7804

Published: Sept. 6, 2024

Herein, we report the enantioselective phosphine-catalyzed β,γ-annulation of electron-poor allenes with bifunctional malonates. The reaction exploits a 2C phosphonium synthon that when accessed using (

Language: Английский

Citations

1
Enantioselective Synthesis of Cyclopentenes by (3+2) Annulation via a 2‐Carbon Phosphonium DOI Creative Commons
Antonia Seitz, Jeremy T. Maddigan‐Wyatt, Jing Cao

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(35)

Published: July 8, 2024

Abstract Herein we report a catalytic enantioselective (3+2) annulation, in which vinyl phosphonium intermediate serves as the 2‐carbon component. The reaction involves an α‐umpolung β‐umpolung coupling sequence, enabled by β‐haloacrylates and chiral enantioenriched phosphepine catalysts. shows good generality, providing access to array of cyclopentenes, with mechanistic studies supporting stereospecific formation which, then undergoes annulation turn over limiting catalyst elimination. Beyond defining new approach these demonstrate that can replace ynoates designs require exclusive umpolung at α‐ β‐positions.

Language: Английский

Citations

0
DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes DOI

Dongqiu Li,

Jiale Wu, Lulu Yang

et al.

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

Published: Dec. 20, 2024

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, use the β- ε-carbons for bond formation, presenting new regiodivergent C4 synthons Lewis base-catalyzed annulations.

Language: Английский

Citations

0