Highly stereoselective titanium-mediated aldol reactions from chiral α-silyloxy ketones. A reliable tool for the synthesis of natural products |
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Authors: | Judit EsteveCarme Jiménez Joaquim NebotJavier Velasco Pedro Romea Fèlix Urpí |
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Institution: | Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain |
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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. |
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Keywords: | Stereoselective reactions Aldol reactions Titanium enolates Chiral ketones Natural product synthesis |
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