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Asymmetric synthesis of aminopyrimidine and cyclic guanidine amino acids

Möschwitzer, Vicki Doreen, Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897 and Redman, James Edward ORCID: https://orcid.org/0000-0001-5492-2869 2013. Asymmetric synthesis of aminopyrimidine and cyclic guanidine amino acids. Tetrahedron Letters 54 (34) , pp. 4526-4528. 10.1016/j.tetlet.2013.06.066

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Abstract

Syntheses of amino acids with aminopyrimidine and cyclic guanidine side chains are described. The synthetic route employed Heck coupling of methyl 2-acetamidoacrylate to 4-methoxybenzyl protected 2-amino-5-iodopyrimidine, followed by Rh(I)-catalyzed asymmetric hydrogenation to afford a chiral protected amino acid. All protecting groups were removed under acidic conditions to afford the amino acid, (S)-2-amino-3-(2-aminopyrimidin-5-yl)propanoic acid, which underwent hydrogenation to afford an amino acid with a six-membered cyclic guanidine side chain.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Amino acid; Aminopyrimidine; Guanidine; Asymmetric hydrogenation
Publisher: Elsevier
ISSN: 0040-4039
Funders: EPSRC
Last Modified: 24 Oct 2022 11:38
URI: https://orca.cardiff.ac.uk/id/eprint/48819

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