Stereoselective C-glycosylation reactions of ribose derivatives: Electronic effects of five-membered ring oxocarbenium ions

Catharine H. Larsen, Brian H. Ridgway, Jared T. Shaw, Deborah M. Smith, K. A. Woerpel

Research output: Contribution to journalArticle

161 Scopus citations

Abstract

The factors controlling the highly α-selective C-glycosylation of ribose derivatives were determined by examining the Stereoselective reactions of 18 ribose analogues differing in substitution at C-2, C-3, and C-4. The lowest energy conformers of the intermediate oxocarbenium ions display the C-3 alkoxy group in a pseudoaxial orientation to maximize electrostatic effects. To a lesser extent, the C-2 substituent prefers a pseudoequatorial position, and the alkyl group at C-4 has little influence on conformational preferences. In all cases, the product was formed by stereoelectronically preferred inside attack on the lowest energy conformer.

Original languageEnglish (US)
Pages (from-to)10879-10884
Number of pages6
JournalJournal of the American Chemical Society
Volume127
Issue number31
DOIs
StatePublished - Aug 10 2005

ASJC Scopus subject areas

  • Chemistry(all)

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