Enantio- and Diastereoselective Synthesis of exo-Peroxyacetals: An Organocatalyzed Peroxyhemiacetalization/oxa-Michael Addition Cascade

Sanjay Maity, Biswajit Parhi, Prasanta Ghorai

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

An unprecedented enantioselective peroxyhemiacetalization/oxa-Michael addition cascade of ortho-formyl homochalcones has been developed using cinchona-alkaloid-based chiral bifunctional organocatalysts to provide cis-configured exo-peroxyacetals, a new class of organic peroxide, in good yields with excellent enantio- and diastereoselectivities. The resulting cis-configured exo-peroxyacetals were converted into the corresponding trans-configured peroxyacetals without affecting the enantioselectivity. Furthermore, the displacement of the peroxide moiety of exo-peroxyacetals with various nucleophiles has been demonstrated to afford 1,3-disubstituted isochromans with high diastereoselectivities and excellent enantioselectivities.

Original languageEnglish (US)
Pages (from-to)7723-7727
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number27
DOIs
StatePublished - Jun 27 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Michael addition
  • asymmetric synthesis
  • heterocycles
  • organocatalysis
  • peroxides

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