Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity

Peter R. Ashton, Patrizia Calcagno, Neil Spencer, Kenneth D.M. Harris*, Douglas Philp

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

(Matrix Presented) The rational design of a bis(phosphine oxide) host which is capable of binding a benzylic amine is presented. The ability of this host to increase the rate of addition of 4-fluorobenzylamine to N-phenylmaleimide is rationalized in terms of the enhancement of the nucleophilicity of the benzylic amine.

Original languageEnglish (US)
Pages (from-to)1365-1368
Number of pages4
JournalOrganic Letters
Volume2
Issue number10
DOIs
StatePublished - May 18 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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