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Title: | Lewis-acid-promoted selective isomerization of oxetanes. New synthetic approach towards γ-chiral alcohols |
Other Titles: | Isomerització selectiva d’oxetans induïda per àcid de Lewis. Nou enfoc sintètic cap a alcohols γ-quirals |
Author: | Rafael Miguel, Sergi |
Director/Tutor: | Riera i Escalé, Antoni Cabré Montesinos, Albert |
Keywords: | Alcohols Àcids de Lewis Isomerització Hidrogenació Treballs de fi de grau Alcohols Lewis acids Isomerization Hydrogenation Bachelor's theses |
Issue Date: | Jun-2019 |
Abstract: | The synthesis of enantiomerically pure compounds is one of the main challenges in organic synthesis. Particularly, γ-chiral alcohols are a valuable chemical motif and a useful building block, especially in the pharmaceutical industry. Even though there are several synthetic methodologies already studied, they offer poor atom economy reactions and there is a need of separation steps, consequently lowering the final yield. For this reason, a new approach would be highly desired. Most promising approaches undergo isomerization reactions that are highly atom economy efficient and generate low to no residues. Still there is not a selective procedure to the isomerization of oxetanes. In this work, a new general and greener synthetic pathway has been developed. This new approach is based on the Lewis-acid-promoted selective isomerization of oxetane rings. Afterwards, the correspondent olefin is subjected to an asymmetric hydrogenation using iridiumbased catalysts. A standard substrate has been tested in order to optimize the methodology. Finally, a broad scope of substrates has been studied to generalize the process |
Note: | Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2019, Tutors: Antoni Riera Escalé, Albert Cabré Montesinos |
URI: | http://hdl.handle.net/2445/138217 |
Appears in Collections: | Treballs Finals de Grau (TFG) - Química |
Files in This Item:
File | Description | Size | Format | |
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TFG_QU Rafael Miguel, Sergi.pdf | 1.15 MB | Adobe PDF | View/Open |
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