An efficient, facile, and general stereoselective synthesis of heterosubstituted alkylidenecyclopropanes

Ahmad Masarwa*, Amnon Stanger, Ilan Marek

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

(Chemical Equation Presented) With just a nudge (in the form of silica gel, an acidic ion-exchange resin, or heating at about 40°C), the acetate derivatives of enantiomerically enriched cyclopropenyl alcohols undergo sigmatropic rearrangement to give alkylidenecyclopropanes with high ee values (see scheme). Similarly, the rearrangement of phosphinite derivatives at room temperature leads to phosphine oxide precursors of unusual chiral phosphine ligands. R1, R2 = alkyl, aryl.

Original languageAmerican English
Pages (from-to)8039-8042
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number42
DOIs
StatePublished - 2007
Externally publishedYes

Keywords

  • Alkylidenecyclopropanes
  • Chiral phosphanes
  • Cyclopropenes
  • Sigmatropic rearrangement
  • Synthetic methods

Fingerprint

Dive into the research topics of 'An efficient, facile, and general stereoselective synthesis of heterosubstituted alkylidenecyclopropanes'. Together they form a unique fingerprint.

Cite this