Asymmetric induction in Diels‐Alder reactions to acrylates derived from chiral sec‐alcohols. Preliminary communication

Wolfgang Oppolzer, Mark Kurth, Daniel Reichlin, Christian Chapuis, Martin Mohnhaupt, Frank Moffatt

Research output: Contribution to journalArticle

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Abstract

Starting from the enantiomerically pure monoterpenes (+)‐pulegone (3), (+)‐limonene (7), (−)‐β‐pinene (9), (+)‐ and (−)‐camphor (13) or (+)‐cholestenone (11) the chiral alcohols 4, 5, 6, 8, 10, 12, 14, 15, 16, 17 et 18 were prepared; their acrylates II underwent a TiCl4‐promoted Diels‐Alder addition to cyclopentadiene Scheme 3, Table giving in a predictable manner either the (2R)‐ or the (2S)‐adducts III with 63 to 88% asymmetric induction.

Original languageGerman
Pages (from-to)2802-2807
Number of pages6
JournalHelvetica Chimica Acta
Volume64
Issue number8
DOIs
StatePublished - 1981
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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