Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols.
Timothy B Clark, K A Woerpel
文献索引:Org. Lett. 8(18) , 4109-12, (2006)
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摘要
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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