Enantioselective N-Heterocyclic Carbene Catalyzed Cyclopentene Synthesis via the β-Azolium Ylide

Lydia Scott, Yuji Nakano, Changhe Zhang, David W. Lupton

Research output: Contribution to journalArticleResearchpeer-review

13 Citations (Scopus)

Abstract

Herein we report the cycloisomerization of electron-poor 1,5-dienes via the β-azolium ylide to give enantioenriched cyclopentenes. The reaction is mediated by a chiral N-heterocyclic carbene (NHC) catalyst, exploits readily available substrates, has good generality (17 examples), and displays excellent enantioselectivity (mostly >94:6). Studies demonstrating the viability of a related dynamic kinetic resolution are reported, as are those with alternate tethers and derivatizations.

Original languageEnglish
Pages (from-to)10299-10303
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number32
DOIs
Publication statusPublished - 6 Aug 2018

Keywords

  • 1,4-addition
  • cyclopentene
  • N-heterocyclic carbenes
  • organocatalysis
  • β-azolium ylide

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