Regioselective annulation of propargyl alcohols with ambident-enols: A Ca(II)-catalyzed trisubstituted benzochromene synthesis

Srinivasarao Yaragorla, Abhishek Pareek, Ravikrishna Dada

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Highly regioselective, 6-endo cyclization between propargyl alcohols and ambident enols such as naphthols, 4-hydroxy coumarin, cyclohexane-1,3-dione, 5,5-dimethylcyclohexane-1,3-dione is described using Ca(OTf)2 under solvent free conditions. The reaction proceeds through a cascade annulation which involves an etherification, Claisen type rearrangement, allene formation and endocyclization. Further, we extended this method to the synthesis of iodo-derivative and demonstrated the reactivity in cross-coupling reactions.

Original languageEnglish (US)
Pages (from-to)4642-4647
Number of pages6
JournalTetrahedron Letters
Volume58
Issue number49
DOIs
StatePublished - Dec 6 2017
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Ltd

Keywords

  • Ambident nucleophiles
  • Benzochromenes
  • Calcium catalysis
  • Claisen rearrangement
  • Propargyl alcohols

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