Access to polyfunctionalized diquinanes, hydrindanes, and decalines via TiCl4 promoted Michael-aldol and Baylis-Hillman reactions |
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Authors: | Ressault Blandine Jaunet Alexis Geoffroy Philippe Goudedranche Sébastien Miesch Michel |
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Affiliation: | Université de Strasbourg, Institut de Chimie, UMR UdS-CNRS 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP296/R8 67008, Strasbourg, France. |
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Abstract: | The addition of 0.5 equiv of TiCl(4) to (cyclo)alkanones tethered to α,β-unsaturated ketones afforded polyfunctionalized diquinanes, hydrindanes, and decalines. These products, resulting from a Michael-aldol or a Baylis-Hillman reaction, can be obtained with high or total diastereoselectivity in moderate to high yields. These scaffolds represent interesting building blocks for the synthesis of complex natural products. |
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