Improving catalyst activity in secondary amine catalysed transformations

John B. Brazier, Timothy J. K. Gibbs, Julian H. Rowley, Leopold Samulis, Sze Chak Yau, Alan R. Kennedy, James A. Platts, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The effect on catalyst performance of altering substituents at the 2-position of the Macmillan imidazolidinone has been examined. Condensation of L-phenylalanine N-methyl amide with acetophenone derivatives results in a series of imidazolidinones whose salts can be used to accelerate the Diels-Alder cycloaddition. Electron withdrawing groups significantly increases the overall rate of cycloaddition without compromise in selectivity. The most effective catalyst was shown to be efficient for a variety of substrates and the applicability of this catalyst to alternative secondary amine catalysed transformations is also discussed.
LanguageEnglish
Pages133-141
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number1
Early online date14 Oct 2014
DOIs
Publication statusPublished - 7 Jan 2015

Fingerprint

Cycloaddition Reaction
Amines
Catalyst activity
amines
Cycloaddition
cycloaddition
catalysts
Catalysts
Phenylalanine
Amides
phenylalanine
Catalyst selectivity
Salts
Electrons
amides
Condensation
condensation
selectivity
salts
Derivatives

Keywords

  • catalyst performance
  • catalyst activity
  • cycloaddition

Cite this

Brazier, John B. ; Gibbs, Timothy J. K. ; Rowley, Julian H. ; Samulis, Leopold ; Yau, Sze Chak ; Kennedy, Alan R. ; Platts, James A. ; Tomkinson, Nicholas C. O. / Improving catalyst activity in secondary amine catalysed transformations. In: Organic and Biomolecular Chemistry. 2015 ; Vol. 13, No. 1. pp. 133-141.
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Improving catalyst activity in secondary amine catalysed transformations. / Brazier, John B.; Gibbs, Timothy J. K.; Rowley, Julian H.; Samulis, Leopold; Yau, Sze Chak; Kennedy, Alan R.; Platts, James A.; Tomkinson, Nicholas C. O.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 1, 07.01.2015, p. 133-141.

Research output: Contribution to journalArticle

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