Enantioselective, organocatalytic oxy-Michael addition to γ/δ-hydroxy-α,β-enones: Boronate-amine complexes as chiral hydroxide synthons

Run Li De, Andiappan Murugan, J R Falck

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Abstract

An organocatalytic, enantioselective oxy-Michael addition to achiral γ- and δ-hydroxy-α,β-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral β-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.

Original languageEnglish (US)
Pages (from-to)46-48
Number of pages3
JournalJournal of the American Chemical Society
Volume130
Issue number1
DOIs
StatePublished - Jan 9 2008

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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