Highly chemo-, enantio-, and regioselective synthesis of α,α-disubstituted furanones by Cu-catalyzed conjugate addition

Kohei Endo, Sayuri Yakeishi, Ryotaro Takayama, Takanori Shibata

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12 Citations (Scopus)

Abstract

A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported. The Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place. Synthetic transformations of furanones represent facile approaches to various cyclic or acyclic compounds bearing a quaternary stereogenic center. Selective chemistry: A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported (see scheme). Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place.

Original languageEnglish
Pages (from-to)8893-8897
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number29
DOIs
Publication statusPublished - 2014 Jul 14

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Keywords

  • addition reactions
  • aluminum
  • asymmetric synthesis
  • copper
  • heterocyclic compounds

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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