Strained cycloalkanols in C–C bond formation reactions: a boon in disguise!

Jha, Neha; Mishra, Pradeep; Kapur, Manmohan

doi:10.1039/d3qo01090b

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01090b

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Strained cycloalkanols in C–C bond formation reactions: a boon in disguise!

Neha Jha¹,

Pradeep Mishra²,

Manmohan Kapur³

Abstract: With a significant prominence in various strain release transformations, the strained cycloalkanols act as ‘n’ carbon synthons in a multitude of diversified reactions. Their ease of formation, along with facile...

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Cited by 9 publications

References 99 publications

(112 reference statements)

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Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions

Han,

Zhan,

Yang

et al. 2024

Eur J Org Chem

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Cycloalkanols ring‐opening transformation is one of the most valuable and wide area of research. Among the numerous methods that have been developed, transition‐metal‐free approaches have attracted great interest from both chemists and pharmacologists. This is largely due to the advantages of being environmentally benign, cost‐effective and operationally simple. Here we provide a comprehensive outline on recent advances in the synthesis of distally substituted ketones and cyclic compounds via ring‐opening transformation of cycloalkanols under transition‐metal‐free conditions.

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Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions

Han,

Zhan,

Yang

et al. 2024

Eur J Org Chem

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Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer

Zhang,

Zhao,

et al. 2025

Chinese Chemical Letters

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Hydroxy Group-Enabled Regio- and Stereoselective Hydroalkylation of Alkynyl Cyclobutanol via Palladium-Catalyzed C–C Bond Activation of Cyclopropanol: A One-Step Access to Vinyl Cyclobutanols

Najiar,

Pati,

Das Adhikari

et al. 2024

Org. Lett.

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The regio-/stereoselective synthesis of vinyl cyclobutanols from alkynyl cyclobutanols is demonstrated. Here, selective C−C bond activation of the cyclopropyl alcohol ring has been achieved in the presence of the cyclobutanol ring. The KIE experiments indicated the noninvolvement of the O−H oxidative addition step in the rate-determining step. Further, the applicability of these vinyl cyclobutanols for the synthesis of 1,4-diketones and 1,6-diketone is demonstrated.

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Strained cycloalkanols in C–C bond formation reactions: a boon in disguise!

Abstract: With a significant prominence in various strain release transformations, the strained cycloalkanols act as ‘n’ carbon synthons in a multitude of diversified reactions. Their ease of formation, along with facile...

Cited by 9 publications

References 99 publications

Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions

Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions

Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer

Hydroxy Group-Enabled Regio- and Stereoselective Hydroalkylation of Alkynyl Cyclobutanol via Palladium-Catalyzed C–C Bond Activation of Cyclopropanol: A One-Step Access to Vinyl Cyclobutanols

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