Asymmetric Brønsted acid-catalyzed Nazarov cyclization of acyclic α-alkoxy dienones

Sadiya Raja, Winai Ieawsuwan, Vadim Korotkov, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

A Brønsted acid-catalyzed asymmetric Nazarov cyclization of acyclic α-alkoxy dienones has been developed. The reaction offers access to chiral cyclopentenones in a highly enantioselective manner. The reaction is complementary to our previously reported Brønsted acid-catalyzed electrocyclization reactions, which provided differently substituted optically active cyclopentenones with a fused tetrahydropyrane ring in good yields and with excellent enantioselectivities. I've got 5 on it! An enantioselective Brønsted acid-catalyzed Nazarov cyclization of acyclic α-alkoxy dienones that affords optically active cyclopentenones in good yields and excellent enantiomeric excess has been developed.

Original languageEnglish (US)
Pages (from-to)2361-2366
Number of pages6
JournalChemistry - An Asian Journal
Volume7
Issue number10
DOIs
StatePublished - Oct 1 2012

Keywords

  • Brønsted acids
  • Nazarov reaction
  • asymmetric synthesis
  • electrocyclizations
  • organocatalysis

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Organic Chemistry

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