Application of the intramolecular azomethine imine cycloaddition to the construction of a novel, orthogonally protected spirodiamino acid scaffold

Roland E. Dolle, Michael C. Barden, Paul E. Brennan, Gulzar Ahmed, Vinh Tran, Douglas M. Ho

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Hydrazone 4 undergoes tandem intramolecular Michael addition - intramolecular azomethine imine cyctoaddition in ethanol at reflux to furnish the tricyclic pyrazoline methyl ester 3 in 75% yield. A five-step conversion of 3 to N1-Alloc-6-(N-Boc-aminomethyl)-1-azaspiro[4.4]nonane-2-acetic acid 1 provides access to a unique tri-functionalized scaffold for combinatorial chemistry.

Original languageEnglish
Pages (from-to)2907-2908
Number of pages2
JournalTetrahedron Letters
Volume40
Issue number15
DOIs
StatePublished - Apr 9 1999
Externally publishedYes

Keywords

  • Azomethine imine
  • Combinatorial chemistry
  • Intramolecular dipolar cycloaddition

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