A completely selective and strongly accelerated Diels-Alder reaction mediated by hydrogen bonding

Russell J. Pearson, Eleftherios Kassianidis, Douglas Philp*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

A Diels-Alder cycloaddition between a furan and a maleimide is presented in which the presence of complementary hydrogen bonding sites dramatically accelerate the reaction and, additionally, ensure that only one of two possible diastereoisomers is formed.

Original languageEnglish (US)
Pages (from-to)4777-4780
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number24
DOIs
StatePublished - Jun 7 2004

Keywords

  • Cycloaddition
  • Diels-Alder
  • Hydrogen-bonding
  • Molecular recognition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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