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

Timothy B. Clark, Keith Woerpel

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)4109-4112
Number of pages4
JournalOrganic Letters
Volume8
Issue number18
DOIs
StatePublished - Aug 31 2006

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triols
Ether
ethers
reactivity
Allylation
Carbonyl compounds
carbonyl compounds
Ketones
aldehydes
Aldehydes
ketones
Functional groups
Copper
insertion
phosphates
silver
copper

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Formation and reactivity of silacyclopropenes derived from siloxyalkynes : Stereoselective formation of 1,2,4-triols. / Clark, Timothy B.; Woerpel, Keith.

In: Organic Letters, Vol. 8, No. 18, 31.08.2006, p. 4109-4112.

Research output: Contribution to journalArticle

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