Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols.

Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols. Research Abstract Details 

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Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols. Abstract Text:

Timothy B Clark,K A Woerpel,

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.

Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols. Publishing Authors By Initials

TB Clark,KA Woerpel,

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Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Organic letters

VOLUME: 8

Page Numbers: 4109-12

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ISSN: 1523-7060

DAY: 31

MONTH: Aug

YEAR: 2006

Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols. Information

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LANGUAGE: eng

NlmUniqueID: 100890393

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Grant and Affiliation Information for Formation and reactivity of silacyclopropenes derived from siloxyalkynes: stereoselective formation of 1,2,4-triols.

AFFILIATION: Department of Chemistry, University of California-Irvine, CA 92697-2025, USA.

Country: United States

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MEDLINETA: Org Lett

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