Organocatalytic Asymmetric Cyclization Reactions with <i>γ</i>‐Hydroxyenones

This review article provides an overview of the recent developments in organocatalytic asymmetric cyclization strategies utilizing γ ‐hydroxyenones. Due to the bifunctional nature of γ ‐hydroxyenones, it is a powerful building block for synthesizing oxygen‐ and nitrogen‐containing heterocycles. The cyclization strategies are systematically categorized based on the nature of the organocatalysts employed: (i) chiral prolinol analogs, which obtain tetrahydrofuran‐fused 3,4‐dihydrocoumarins and 2,3,4‐trisubstituted tetrahydrofurans; (ii) chiral bifunctional squaramides, affording diverse spirocyclic frameworks such as spiro‐tetrahydrofuran‐pyrazolones, morpholinones, and oxindole‐derived systems; (iii) chiral bifunctional thioureas, which forms 1,3‐dioxolanes, oxazolidines, and cyclic acetals; (iv) multifunctional modular organocatalysts, affording enantioenriched α , β ‐disubstituted γ ‐butyrolactones; and (v) other chiral organocatalysts which cannot be grouped in previous categories such as Song's chiral oligoethylene glycol as a cation‐binding catalyst leads to the generation of chiral 1,4,2‐dioxazinanes.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-06-29
DOI
https://doi.org/10.1002/ejoc.202500482
Citations
1
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
0.94
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article

Organocatalytic Asymmetric Cyclization Reactions with γ‐Hydroxyenones

Subhas Chandra Pan, Megha Balha
1 citations
European Journal of Organic Chemistry
Axial and Atropisomeric Chirality Synthesis
0.94
article

Organocatalytic Asymmetric Cyclization Reactions with γ‐Hydroxyenones

Subhas Chandra Pan, Megha Balha
article en
1 citations

Abstract

This review article provides an overview of the recent developments in organocatalytic asymmetric cyclization strategies utilizing γ ‐hydroxyenones. Due to the bifunctional nature of γ ‐hydroxyenones, it is a powerful building block for synthesizing oxygen‐ and nitrogen‐containing heterocycles. The cyclization strategies are systematically categorized based on the nature of the organocatalysts employed: (i) chiral prolinol analogs, which obtain tetrahydrofuran‐fused 3,4‐dihydrocoumarins and 2,3,4‐trisubstituted tetrahydrofurans; (ii) chiral bifunctional squaramides, affording diverse spirocyclic frameworks such as spiro‐tetrahydrofuran‐pyrazolones, morpholinones, and oxindole‐derived systems; (iii) chiral bifunctional thioureas, which forms 1,3‐dioxolanes, oxazolidines, and cyclic acetals; (iv) multifunctional modular organocatalysts, affording enantioenriched α , β ‐disubstituted γ ‐butyrolactones; and (v) other chiral organocatalysts which cannot be grouped in previous categories such as Song's chiral oligoethylene glycol as a cation‐binding catalyst leads to the generation of chiral 1,4,2‐dioxazinanes.

European Journal of Organic ChemistryVol. 28(32)
Indian Institute of Technology Guwahati (IN), GITAM University (IN)
Openalex Percentile: Top 24%
Axial and Atropisomeric Chirality Synthesis
0.94
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Organocatalytic Asymmetric Cyclization Reactions with <i>γ</i>‐Hydroxyenones — Subhas Chandra Pan, Megha Balha · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS