Stereoelectronic Model to Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

Matthew G. Beaver, Trixia M. Buscagan, Olga Lavinda, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.

Original languageEnglish (US)
Pages (from-to)1816-1819
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number5
DOIs
StatePublished - Jan 26 2016

Keywords

  • carbocations
  • carbohydrates
  • conformational analysis
  • electrostatic effects
  • stereoselectivity

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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