Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

R Robiette, M Conza, VK Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

34 Citations (Scopus)

Abstract

Diastereoselectivity in reactions of aryl-stabilised ammonium ylides are highly sensitive to the nature of the amine and the ylide substituent. DFT calculations are consistent with a mechanism in which reversibility in betaine formation [despite the high energy (and therefore instability) of ammonium ylides] is finely balanced due to the high barrier to ring closure.

Original languageEnglish
Pages (from-to)621-623
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number4
DOIs
Publication statusPublished - 21 Feb 2006

Keywords

  • IN-SITU GENERATION
  • ORGANOCATALYTIC CYCLOPROPANATION
  • CARBONYL-COMPOUNDS
  • DIAZO-COMPOUNDS
  • SULFUR YLIDES
  • SCOPE

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