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

Organic & Biomolecular Chemistry
Lynne GilfillanAndrew Sutherland

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.

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Citations

Oct 8, 2016·Organic & Biomolecular Chemistry·Alexander H Harkiss, Andrew Sutherland
Jan 21, 2020·Chemical Communications : Chem Comm·Jonathan D BellAndrew Sutherland
Jun 29, 2021·Organic & Biomolecular Chemistry·Rochelle McGroryAndrew Sutherland
Feb 7, 2019·The Journal of Organic Chemistry·Alexander H HarkissAndrew Sutherland
Jul 26, 2019·The Journal of Organic Chemistry·Jonathan D BellAndrew Sutherland

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