Enantio- and periselective nitroalkene diels-alder reactions catalyzed by helical-chiral hydrogen bond donor catalysts

Zhili Peng, Maurice J. Narcis, Norito Takenaka

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Helical-chiral double hydrogen bond donor catalysts promote the nitroalkene Diels-Alder reaction in an enantio- and periselective manner. This represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via LUMO-lowering catalysis. To gain an insight into this new process, the substrate scope of our catalyst was investigated by exploiting readily available 5-substituted pentamethylcyclopentadienes. The catalyst was found to tolerate dienes with different steric demands as well as dienes substituted with heteroatoms. The synthetic utility of 5-substituted pentamethylcyclopentadienes is rather limited, and thus we have developed a three-step route to 1,4,5,5-tetrasubstituted cyclopentadienes from commercially available ketones.

Original languageEnglish (US)
Pages (from-to)9982-9998
Number of pages17
JournalMolecules
Volume18
Issue number8
DOIs
StatePublished - Aug 2013

Keywords

  • Asymmetric catalysis
  • Diels-Alder reaction
  • Helical chirality
  • Nitroalkene

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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