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New access to racemic β3-amino acids

Michał Nejman, Anna Śliwińska and Andrzej Zwierzak*

*Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland

M. Nejman, A. Śliwińska, A. Zwierzak, Tetrahedron, 2005, 61, 8536-8541.

DOI: 10.1016/j.tet.2005.04.077

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A base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl sulfones in tetrahydrofuran followed by hydrolysis of the adducts in refluxing 6 M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in high yield and excellent purity.

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Key Words

Michael-type addition, Decarboxylation, N-Boc imines, Diethyl malonate, tert-Butyl carbamates, β-Amino acids

ID: J72-Y2005-3020