Diastereoselective Synthesis of Seven-Membered-Ring trans-Alkenes from Dienes and Aldehydes by Silylene Transfer |
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| Authors: | Margaret A Greene Michel Prévost Joshua Tolopilo K A Woerpel |
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| Institution: | Department of Chemistry, New York University , 100 Washington Square East, New York, New York 10003, United States. |
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| Abstract: | Silver-catalyzed silylene transfer to alkenes forms vinylsilacyclopropanes regioselectively. These allylic silanes undergo additions to aldehydes to form seven-membered-ring trans-alkenes with high diastereoselectivity. The high reactivity of the trans-alkenes is evidenced by their formal 1,3]-sigmatropic rearrangement reactions and the rapid additions of oxygen-hydrogen bonds across the carbon-carbon double bonds. |
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