Mechanism of triflimide-catalyzed [3,3]-sigmatropic rearrangements of N-allylhydrazones—predictions and experimental validation

Osvaldo Gutierrez, Regan J. Thomson*, Dean J. Tantillo

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Computational analysis of the triflimide catalyzed [3,3]-sigmatropic rearrangement of N-allylhydrazones, using density functional theory calculations, is reported. Key mechanistic insight was obtained and predictions derived therefrom were confirmed experimentally through temperature dependence studies. The computational results have led to the development of electron deficient N-allylhydrazones capable of reacting under mild reaction conditions. Application of the rearrangement to form a new sp3 stereogenic center is reported for the first time.

Original languageEnglish (US)
Pages (from-to)3997-4003
Number of pages7
JournalChemical Science
Volume4
Issue number10
DOIs
StatePublished - Aug 26 2013

ASJC Scopus subject areas

  • Chemistry(all)

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