Enzyme-like control of carbocation deprotonation regioselectivity in supramolecular catalysis of the nazarov cyclization

Courtney J. Hastings, Mikael P. Backlund, Robert G. Bergman, Kenneth N. Raymond

Research output: Contribution to journalArticlepeer-review

Abstract

The kinetically controlled, regioselective deprotonation of cyclopentenyl cations is mediated by encapsulation within a metal-ligand assembly. The regiochemistry of the deprotonation step determines which one of two possible products is formed. Moreover, subtle differences in the stereochemistry of the encapsulated cation switch the selectivity of this process (see scheme).

Original languageEnglish (US)
Pages (from-to)10570-10573
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number45
DOIs
StatePublished - Nov 4 2011
Externally publishedYes

Keywords

  • cage compounds
  • carbocations
  • electrocyclic reactions
  • homogeneous catalysis
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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