Stereoselective synthesis of silacyclohexanols by silicon tethered Type II ene cyclisation

Vinyl silane precursors for intramolecular ene reaction were prepared either by sequential organometallic substitution of appropriate silyl halides or by ring opening of oxasilacyclopentanes with 2-propenyllithium. The oxasilacyclopentane intermediates were prepared by free-radical cyclisation, intr...

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מידע ביבליוגרפי
Main Authors: Robertson, J, O'Connor, G, Sardharwala, T, Middleton, D
פורמט: Journal article
שפה:English
יצא לאור: 2000
תיאור
סיכום:Vinyl silane precursors for intramolecular ene reaction were prepared either by sequential organometallic substitution of appropriate silyl halides or by ring opening of oxasilacyclopentanes with 2-propenyllithium. The oxasilacyclopentane intermediates were prepared by free-radical cyclisation, intramolecular hydrosilylation, or intramolecular Diels-Alder reaction. Treatment of the ene precursors with methylaluminium dichloride resulted in the formation of silacyclohexanols with high stereoselectivity. (C) 2000 Elsevier Science Ltd.