Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans

Dorine Belmessieri, Alix De La Houpliere, Ewen D.D. Calder, James E. Taylor, Andrew D. Smith

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r. syn/anti, 99% eesyn), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r.syn/anti, 99% eeanti). You can have it both ways! A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported, giving products with high d.r. and ee (see scheme).

Original languageEnglish
Pages (from-to)9762-9769
Number of pages8
JournalChemistry - A European Journal
Volume20
Issue number31
Early online date2 Jul 2014
DOIs
Publication statusPublished - 28 Jul 2014

Keywords

  • asymmetric catalysis
  • cinchona alkaloid
  • isothiourea
  • Michael addition
  • organocatalysis
  • oxygen heterocycles
  • stereodivergent

ASJC Scopus subject areas

  • Chemistry(all)

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