Stereoselective TiCl4-Mediated Aldol Reactions Starting from Acylsilanes

A simple and efficient method for the preparation of β‐hydroxyacylsilanes has been developed through a TiCl4‐mediated aldol reaction. A selection of Lewis acids has been assessed, and other parameters such as solvent and temperature have been optimized. These aldol reactions occur under mild conditi...

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Veröffentlicht in:European journal of organic chemistry 2015-02, Vol.2015 (4), p.840-846
Hauptverfasser: Marri, Gangababu, Reddy, J. Satyanarayana, Ruiz, Johal, Das, Saibal, Grée, René
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Sprache:eng
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Zusammenfassung:A simple and efficient method for the preparation of β‐hydroxyacylsilanes has been developed through a TiCl4‐mediated aldol reaction. A selection of Lewis acids has been assessed, and other parameters such as solvent and temperature have been optimized. These aldol reactions occur under mild conditions and furnish a selection of β‐hydroxy acylsilanes in fair‐to‐good yields with high syn selectivities (up to 99 %). A new, simple and efficient method has been developed for the preparation of β‐hydroxyacylsilanes through a Lewis acid mediated aldol condensation. The use of TiCl4 under optimized reaction conditions allows the preparation of the target molecules in fair‐to‐good yields with excellent syn selectivities.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201403263