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Issue 15, 2015
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Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones

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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.

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

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Publication details

The article was received on 23 Feb 2015, accepted on 10 Mar 2015 and first published on 10 Mar 2015


Article type: Paper
DOI: 10.1039/C5OB00364D
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Citation: Org. Biomol. Chem., 2015,13, 4514-4523
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    Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones

    L. Gilfillan, R. Artschwager, A. H. Harkiss, R. M. J. Liskamp and A. Sutherland, Org. Biomol. Chem., 2015, 13, 4514
    DOI: 10.1039/C5OB00364D

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