Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate

Young Ok Ko, Yu Sung Chun, Youngmee Kim, Sung Jin Kim, Hyunik Shin, Sang Gi Lee

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

A novel tandem one-pot method for the synthesis of α-aminomethylene- γ-butyrolactone derivatives has been developed through the regioselective epoxide opening reactions with the Blaise reaction intermediates, generated by the reaction of a Reformatsky reagent with nitriles. Formation of a modified Blaise reaction intermediate by the addition of a stoichiometric amount of n-BuLi followed by slow addition of epoxide is required for the good yield of γ-butyrolactones.

Original languageEnglish
Pages (from-to)6893-6896
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number52
DOIs
StatePublished - 29 Dec 2010

Keywords

  • Blaise reaction intermediate
  • Butyrolactone
  • Epoxide opening
  • Regioselectivity
  • Tandem reaction

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