Calcium(II)‐Catalyzed Synthesis of Sulfoximinocyclopentenones DOI Creative Commons
Vincent Gandon, Aurélien Alix, Nicolas George

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract A series of 4‐sulfoximinocyclopent‐2‐en‐1‐ones was prepared in 35 to 99% yield through a calcium(II)‐catalyzed aza‐Piancatelli reaction, including enantioenriched form. Depending on their substitution pattern, diverse diastereoselective chemical transformations can be applied these scaffolds, allowing access cyclopentane derivatives. This study opens synthetic routes cyclopentane‐based scaffolds and also paves the way for exploration associated space drug discovery.

Language: Английский

One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction to access 5-quaternary-4-amidocyclopent-2-enones and 2-quaternary-3-amidoindanones DOI

Yue‐Hong Hu,

Yuting Chen,

Zhi‐Juan He

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A one-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction has been explored for the first time, facilitating synthesis of unprecedented 2,3-disubstituted-5-quaternary-4-amidocyclopent-2-enone and 2-quaternary-3-amidoindanones. This transformation features convenient operation, good yields (up to 70%), excellent diastereoselectivity 20 : 1). The proposed mechanism is supported by some experimental results.

Language: Английский

Citations

1
Multicomponent Modular Synthesis of Chiral Bicyclic Bridged Compounds via an Alkenylfuran-Based Acylation/Rearrangement/Cyclization Sequence DOI

Yu Tian,

H. Tao,

Kexin Yang

et al.

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

Published: Jan. 26, 2025

The catalytic asymmetric multicomponent acylation/rearrangement/cyclization of alkenylfurans with acyl oxime esters/arylamines or esters/arylamines/hydroxylamine has been developed. This method employs synergistic photoredox/Brønsted acid catalysis, enabling the efficient and versatile synthesis multifunctionalized [3.2.1] [4.2.1] bicyclic bridged compounds in high yields excellent diastereo- enantioselectivities.

Language: Английский

Citations

0
Stereoselective Access to Spiro-isoindolinone Scaffolds via Catalytic Asymmetric aza-Piancatelli Rearrangement DOI
Ling Yu, Yurong Tang,

Xukun Nie

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7667 - 7671

Published: Aug. 29, 2024

A chiral Brønsted acid catalyzed asymmetric aza-Piancatelli rearrangement of 3-furyl-3-hydroxyisoindolinones with anilines has been developed, enabling the divergent construction spiro-cyclopentenone-isoindolinones in high yields excellent diastereo- and enantioselectivities even under a low catalyst loading 0.5 mol%.

Language: Английский

Citations

3
Calcium(II)‐Catalyzed Synthesis of Sulfoximinocyclopentenones DOI Creative Commons
Vincent Gandon, Aurélien Alix, Nicolas George

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract A series of 4‐sulfoximinocyclopent‐2‐en‐1‐ones was prepared in 35 to 99% yield through a calcium(II)‐catalyzed aza‐Piancatelli reaction, including enantioenriched form. Depending on their substitution pattern, diverse diastereoselective chemical transformations can be applied these scaffolds, allowing access cyclopentane derivatives. This study opens synthetic routes cyclopentane‐based scaffolds and also paves the way for exploration associated space drug discovery.

Language: Английский

Citations

1