Lithiation and reactions of stilbene oxides: Synthetic utility

Saverio Florio, Varinder K Aggarwal, Antonio Salomone

Research output: Contribution to journalArticle (Academic Journal)peer-review

39 Citations (Scopus)

Abstract

The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.

Translated title of the contributionLithiation and Reactions of Stilbene Oxides: Synthetic Utility
Original languageEnglish
Pages (from-to)4191-4194
Number of pages4
JournalOrganic Letters
Volume6
Issue number23
DOIs
Publication statusPublished - 11 Nov 2004

Keywords

  • STEREOSPECIFIC SYNTHESIS
  • OXIRANYL ANION
  • STEREOSELECTIVE SYNTHESIS
  • METALATED EPOXIDES
  • CARBONYL-COMPOUNDS
  • ORGANIC-SYNTHESIS
  • HEMIBREVETOXIN B
  • OXAZOLINYLOXIRANES
  • EPOXIDATION
  • CYCLIZATION

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