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Synthesis of protected 1,3-diols and 1,2-diols via C–H activation processes

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Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2026, Tutor: Xavier Ariza Piquer

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This work investigates the synthesis of protected 1,3- and 1,2-diols through Rh(III)-catalysed C–H activation processes, focusing on the intramolecular cyclisation of hemiacetals of bishomoallylic alcohols and exploring a new approach using homoallylic alcohols.
The study is framed within the ongoing research efforts in our research group, aimed at the development of novel and efficient synthetic methodologies to access 1,3-diol and 1,2-diol motifs. Given the recurrent presence of these structural units in natural products, pharmaceuticals, and other bioactive compounds, the development of efficient and stereoselective synthetic methodologies remains a fundamental challenge in organic chemistry.
The synthetic strategy explored is based on the in situ formation of hemiacetals from different alcohols and propanal, a process that involves a hemiacetal formation equilibrium that is key for obtaining the desired compounds. This synthetic route avoids the use of prefunctionalised substrates and enables the direct formation of protected cis-1,3-diols and 1,2-diols through the generation of sixand five-membered cyclic intermediates. The influence of substrate structure, particularly the differences among various bishomoallylic alcohols, on reactivity, cyclisation efficiency, and stereochemical outcome has been studied, and for the first time within the research group, experiments using a primary homoallylic alcohol have been carried out.
Hemiacetals of bishomoallylic alcohols exhibit a greater tendency to undergo cyclisation, which is attributed to their increased conformational flexibility, favouring hemiacetal formation and intramolecular attack on the π-allyl–Rh intermediate. Conformational analysis allows the observed diastereoselectivity to be rationalised, highlighting a preference for chair conformations in which the bulkier substituents occupy equatorial positions.

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Synthesis of protected 1,3-diols and 1,2-diols via C–H activation processes

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Síntesi d’1,3-diols i 1,2-diols protegits via processos activació C–H