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Highly stereoselective titanium-mediated aldol reactions from chiral α-silyloxy ketones. A reliable tool for the synthesis of natural products
Authors:Judit EsteveCarme Jiménez  Joaquim NebotJavier Velasco  Pedro Romea  Fèlix Urpí
Institution:Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain
Abstract:Chiral α-silyloxy ketones participate in highly stereoselective TiCl4-mediated aldol reactions that afford diastereomerically pure syn-syn adducts in high yield irrespective of the R1 and R2 substituents flanking the carbonyl or the silicon protecting group. Further manipulation of the resulting aldol adducts provide in a straightforward manner highly functionalized fragments that facilitate the synthesis of natural products.
Keywords:Stereoselective reactions  Aldol reactions  Titanium enolates  Chiral ketones  Natural product synthesis
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