Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis

Glenn M. Sammis, Eric M. Flamme, Hao Xie, Douglas M. Ho, Erik J. Sorensen

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

A new 1-hydrazinodiene (1) has been developed and utilized in Lewis acid catalyzed, intermolecular Diels-Alder reactions with various electron-deficient alkenes. The hydrazine can then be deprotected, and a molecule of methanesulfinic acid is eliminated to provide a putative diazene intermediate (4), which then spontaneously undergoes a suprafacial 1,5-sigmatropic shift to yield stereochemically complex cyclohexenes. This method has been applied to the synthesis of a constitutionally and stereochemically complex decalin derivative.

Original languageEnglish (US)
Pages (from-to)8612-8613
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number24
DOIs
StatePublished - Jun 22 2005

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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