Cyclopropanol Chemistry and Synthetic Methodologies
Summary
Cyclopropanols are three-membered carbocyclic alcohols distinguished by pronounced ring strain that renders their C–C bonds highly susceptible to cleavage under mild conditions. This intrinsic reactivity has been harnessed in diverse synthetic approaches to introduce carbonyl, heterocyclic and polyfunctional scaffolds. Key strategies include metal-catalysed ring-opening carbonylations, radical-mediated cyclizations and enolate-like transformations via homoenolate intermediates. Such methodologies have enabled efficient assembly of complex natural products, heterocycles and drug-like molecules, demonstrating the global importance of cyclopropanol chemistry in medicinal chemistry and materials science. Advances have focused on improving regio- and stereocontrol, developing redox-neutral protocols and exploiting cascade or divergent reaction sequences. Together, these developments offer versatile platforms for diversity-oriented synthesis and late-stage functionalisation of bioactive frameworks.
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Cyclopropanol Chemistry and Synthetic Methodologies publication trend
The graph below shows the total number of articles in cyclopropanol chemistry and synthetic methodologies across all publications each year (not limited to Nature Index journals).
Technical terms
Cyclopropanol: A three-membered ring alcohol with high ring strain that facilitates C–C bond cleavage under mild conditions.
Ring‐opening carbonylation: A metal-catalysed transformation combining C–C bond cleavage of a cyclopropanol with CO insertion to yield ketones or esters.
Homoenolate: A nucleophilic species formed by ring opening of a cyclopropanol, resembling an enolate but bearing the negative charge one carbon further from a carbonyl.
Lactonization: Cyclisation process in which a hydroxyl group reacts intramolecularly with a carbonyl to form a cyclic ester (lactone).
α-Hydroxycyclopropanol: A cyclopropanol bearing an adjacent hydroxyl substituent, often employed in divergent ring-opening cyclisations.
References
- Ten-Step Total Synthesis of (±)-Phaeocaulisin A Enabled by Cyclopropanol Ring-Opening Carbonylation. Journal of the American Chemical Society (2024).
- Divergent synthesis of δ-valerolactones and furanones via palladium or copper-catalyzed α-hydroxycyclopropanol ring opening cyclizations. Chemical Communications (2024).
- Synthesis of Vicinal anti-Amino Alcohols from N-tert-Butanesulfinyl Aldimines and Cyclopropanols. The Journal of Organic Chemistry (2024).
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