Practical asymmetric approach to medium-sized carbocycles based on the combination of two ru-catalyzed transformations and a lewis Acid-induced cyclization |
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Authors: | López Fernando Castedo Luis Mascareñas José L |
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Institution: | Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain. |
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Abstract: | Reaction: see text] Ruthenium-catalyzed coupling of allyl ethyl ether to optically active 1-trimethylsilyl-1-alkyn-3-ols, followed by in situ ketalization and Lewis-acid-induced cyclization, affords enantiomerically pure 1,5-oxygen-bridged eight- and nine-membered carbocycles. Opening of the oxygen bridge under basic or electron transfer conditions provides optically pure medium-sized carbocycles, products that are difficult to construct using other currently available methodologies. |
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