A hypervalent iodide-initiated fragment coupling cascade of N-allylhydrazones

Kelly E. Lutz, Regan James Thomson

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

Highway to the hydrazone: A hypervalent iodide initiated cascade process enables the rapid union of an aldehyde, an allylic hydrazide, and an alcohol (see scheme; Pv=pivaloyl). This process affords a diverse range of functionalized ether adducts, while simultaneously generating a stereodefined alkene and two new vicinal stereocenters. The use of chiral non-racemic hydrazines and alcohols offers a rapid entry to complex "natural product-like" structures.

Original languageEnglish (US)
Pages (from-to)4437-4440
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number19
DOIs
StatePublished - May 2 2011

Keywords

  • cascade reactions
  • hydrazones
  • hypervalent iodide reagents
  • stereoselective synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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