In situ generation and nucleophilic capture of 1,n-dial equivalents from 1,n-dioates (α,ω-diesters)

Thomas R Hoye, Lucas C. Kopel, Troy D. Ryba

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

A procedure is described for the in situ generation of functional equivalents of glutaric, succinic, and malonic dialdehydes. DIBAL-H reduction of the corresponding 1,n-dioates followed by in situ addition of a nucleophilic trapping agent allows for one-pot, bidirectional homologation. Olefination and Grignard addition classes of reactions are specifically demonstrated.

Original languageEnglish (US)
Pages (from-to)1572-1574
Number of pages3
JournalSynthesis
Issue number10
DOIs
StatePublished - May 15 2006

Keywords

  • Hydrides
  • Nucleophilic additions
  • Reductions
  • Tandem reactions
  • Wittig reactions

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