Controlling selectivity for cycloadditions of nitrones and alkenes tethered by benzimidazoles: Combining experiment and theory

Oping Meng, Selina C. Wang, James C. Fettinger, Mark J. Kurth, Dean J. Tantill

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Herein we describe a combined experimental/theoretical study on the effects of substituents on regio- and stereoselectivity in intramolecular 1,3-dipolar cycloadditions of nitrones and alkenes tethered by benzimidazoles. By employing a large substituent at position R2 or R3, complete selectivity was achieved for either the fused or bridged cycloadduct, respectively. In addition, these cycloadducts were formed as single diastereomers in all of the cycloadditions examined. copy; Wiley-VCH Verlag GmbH & Co. KGaA.

Original languageEnglish (US)
Pages (from-to)1578-1584
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number10
DOIs
StatePublished - Apr 2009

Keywords

  • Cycloaddition
  • Nitrones
  • Quantum chemical calculations
  • Stereoselectivity
  • Substituent eff'ects
  • Transition states

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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