High diastereoselectivity in the yang photocyclization via remote hydrogen abstraction reaction

Mi Jang, Bong Ser Park

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

1-Benzoyl-1-(o-alkoxyphenyl)cyclopropanes undergo Yang photocyclization to form dihydrobenzopyranols in a stereospecific manner. The cyclopropyl group at alpha position to carbonyls gives not only a bias in the most stable geometries of the starting ketones but also conformational restriction on geometries of biradical intermediates. More importantly, intramolecular hydrogen bonds seem to give an additional effect on conformational control of the biradical reactivity.

Original languageEnglish
Pages (from-to)1509-1514
Number of pages6
JournalBulletin of the Korean Chemical Society
Volume37
Issue number9
DOIs
StatePublished - 1 Sep 2016

Keywords

  • Benzohydropyranol
  • Diastereoselectivity
  • Photochemistry
  • Yang photocyclization
  • ϵ-Hydrogen abstraction

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