Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols |
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Authors: | Clark Timothy B Woerpel K A |
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Institution: | Department of Chemistry, University of California-Irvine, CA 92697-2025, USA. |
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Abstract: | Silver phosphate-catalyzed silylene transfer to siloxyalkynes provided silacyclopropenes possessing a silyl enol ether functional group. Copper-catalyzed insertions of carbonyl compounds afforded the corresponding oxasilacyclopentenes. The embedded silyl enol ether functionality was treated with various aldehydes and a catalytic amount of Sc(OTf)3 to provide dioxasilacycloheptanones, which resulted from an aldol addition/rearrangement. Stereoselective reduction or allylation of the cyclic ketone, followed by n-Bu4NF deprotection, provided high yields of 1,2,4-triols possessing four contiguous stereocenters. |
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