Dynamic Kinetic Spiroketalization/Oxa-Michael Addition Cascade of Alkoxyboronates and Peroxyacetals: Enantio- and Diastereoselective Synthesis of Benzannulated Spiroketals

Abhisek Midya, Sanjay Maity, Prasanta Ghorai

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A unified dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of an aromatic ketone tethered to an alkoxyboronate and an enone moiety has been developed using cinchona alkaloid based amino-thiourea/squaramide organocatalysts to provide isobenzofuran-based benzannulated spiroketals with high diastereoselectivities and excellent enantioselectivities. Further, a dynamic kinetic peroxy-hemiacetalization/dynamic kinetic spiroketalization/enantioselective oxa-Michael addition cascade of the above substrates provides the corresponding exo-peroxy-benzannulated spiroketals with outstanding enantio- and diastereoselectivities.

Original languageEnglish (US)
Pages (from-to)11216-11220
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number47
DOIs
StatePublished - Aug 22 2017

Keywords

  • asymmetric synthesis
  • benzannulated spiroketals
  • organocatalysis
  • oxa-Michael addition
  • peroxy spiroketals
  • spiroketals

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