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

25 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

Bibliographical note

Funding Information:
This work has been funded by CSIR, New Delhi and IISER Bhopal. S.M. and B.P. thank UGC and CSIR, respectively, New Delhi, India for the fellowship. We are thankful to Mr. L. M. Jha and Ms. A. Upadhyay for the crystal analysis. The support from Mr. Barnala Ravindra (IISER-B) is acknowledged.

Keywords

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

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