Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects

Vi Tuong Tran, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

A series of fused-bicyclic acetals containing a disiloxane ring was investigated to evaluate the source of selectivity in silyl-protected 2-deoxyribose systems. The disiloxane ring unexpectedly enables the diaxial conformer of the cation to be stabilized by an electronegative atom at C-3. This low energy conformer subsequently undergoes stereoelectronically controlled nucleophilic addition to give substituted tetrahydrofurans with high diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)6609-6621
Number of pages13
JournalJournal of Organic Chemistry
Volume78
Issue number13
DOIs
StatePublished - Jul 5 2013

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Ions
Furans
Deoxyribose
Acetals
Cations
Atoms
disiloxane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects. / Tran, Vi Tuong; Woerpel, Keith.

In: Journal of Organic Chemistry, Vol. 78, No. 13, 05.07.2013, p. 6609-6621.

Research output: Contribution to journalArticle

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