Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones

Lynne Gilfillan, Raik Artschwager, Alexander H. Harkiss, Rob M. J. Liskamp, Andrew Sutherland*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

A synthetic approach for the preparation of a new class of highly conjugated unnatural α-amino acids bearing a 5-arylpyrazole side-chain has been developed. Horner–Wadsworth–Emmons reaction of an aspartic acid derived β-keto phosphonate ester with a range of aromatic aldehydes gave β-aryl α,β-unsaturated ketones. Treatment of these with phenyl hydrazine followed by oxidation allowed the regioselective synthesis of pyrazole derived α-amino acids. As well as evaluating the fluorescent properties of the α-amino acids, their synthetic utility was also explored with the preparation of a sulfonyl fluoride derivative, a potential probe for serine proteases.
Original languageEnglish
Pages (from-to)4514-4523
Number of pages10
JournalOrganic & Biomolecular Chemistry
Volume15
Early online date10 Mar 2015
DOIs
Publication statusPublished - 21 Apr 2015

Keywords

  • organic chemistry
  • organic synthesis
  • synthetic utility

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