Control of Si and Z/E Stereochemistry via Si-Enantioconvergent and Z/E-Selective Catalysis
Optical isomerism at stereogenic centers and geometrical isomerism in alkenes are foundational concepts in stereochemistry. Achieving precise control over Z and E configurations in alkene synthesis has long posed a significant challenge in synthetic chemistry, especially when simultaneous enantiosel...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/489066 |
| Acceso en línea: | http://hdl.handle.net/2072/489066 https://doi.org/10.31635/ccschem.025.202506802 |
| Access Level: | acceso abierto |
| Palabra clave: | Química 54 |
| Sumario: | Optical isomerism at stereogenic centers and geometrical isomerism in alkenes are foundational concepts in stereochemistry. Achieving precise control over Z and E configurations in alkene synthesis has long posed a significant challenge in synthetic chemistry, especially when simultaneous enantioselectivity is required [(Z,R), (Z,S), (E,R), (E,S)]. In this study, we employed Si-stereogenic vinylsilanes as a model to demonstrate the enantioconvergent synthesis of Si-stereogenic centers and the Z/E-selective synthesis of alkenes within a unified catalytic system. A series of bifunctional chiral silanes, featuring both a vinyl group and a Si–O moiety, were synthesized successfully in high yields with excellent enantioselectivity and Z/E selectivity. This achievement was made possible through an enantioconvergent Si–H/O–H coupling reaction involving racemic alkynyl monohydrosilanes and simple alcohols. The appropriate control of reaction time allows the convenient assembly of Si-stereogenic cis- or trans-vinylsilanes. |
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