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Asymmetric synthesis of aminopyrimidine and cyclic guanidine amino acids

Möschwitzer, Vicki Doreen, Kariuki, Benson and Redman, James Edward 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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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: 04 Jun 2017 05:08

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