Formalizing the mechanism of the allylic substitution reaction (SN'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes

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Abstract

We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the SN' reaction and allows prediction of its stereochemical outcome.

Original languageEnglish
Pages (from-to)308-333
Number of pages26
JournalARKIVOC
Volume2018
Issue number5
DOIs
Publication statusPublished - 7 Jul 2018

Keywords

  • Aryl cyclopentanes
  • Benzyl selenides
  • Se/Li exchange
  • SN' reaction
  • Stereospecific carbocyclization

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