Spirodiepoxides: Heterocycle synthesis and mechanistic insight

Stephen D. Lotesta, Sezgin Kiren, Ronald R. Sauers, Lawrence Williams

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

(Chemical Equation Presented) In concert but out of sync: Reactions of spirodiepoxides (SDEs) with an amide, amidine, and thioamide and the first crystal structure of an SDE are reported (see scheme for reaction with amide; DMDO = 2,2-dimethyldioxirane). Nucleophilic SDE opening is rationalized in terms of a reactivity continuum involving the concerted, asynchronous opening of both epoxides, which is facilitated by coordination to the oxygen atom destined to become the hydroxy group.

Original languageEnglish (US)
Pages (from-to)7108-7111
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number37
DOIs
StatePublished - Oct 3 2007

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Allenes
  • Nitrogen heterocycles
  • Reaction mechanism
  • Spirodiepoxides

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