Enantiomerically pure cyclopropenylcarbinols as a source of chiral alkylidenecyclopropane derivatives

Samah Simaan*, Ahmad Masarwa, Philippe Bertus, Ilan Marek

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

82 Scopus citations

Abstract

(Chemical Equation Presented) The straightforward approach: The copper-catalyzed carbomagnesiation reaction of chiral cyclopropenylcarbinol derivatives, obtained through kinetic resolution of secondary allylic alcohols, leads to the preparation of enantiomerically pure alkylidenecyclopropane derivatives. The reaction mechanism is composed of a syn carbometalation followed by a syn elimination reaction.

Original languageAmerican English
Pages (from-to)3963-3965
Number of pages3
JournalAngewandte Chemie - International Edition
Volume45
Issue number24
DOIs
StatePublished - 12 Jun 2006
Externally publishedYes

Keywords

  • Cyclopropanes
  • Elimination
  • Grignard reagents
  • Homogeneous catalysis
  • Strained molecules

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