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

Vi Tuong Tran, K. A. 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

ASJC Scopus subject areas

  • Organic Chemistry

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