DOI: 10.1039/A809586H
(Paper)
J. Chem. Soc., Perkin Trans. 1, 1999, 1567-1570
New convenient access to thioesters of α-amino acids from N,N-disubstituted 2-aminoalk-2-enals
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Alexandre Yu. Rulev, Lyudmila I. Larina, Natalia A. Keiko and Mikhail G. Voronkov
Abstract
N,N-Disubstituted 2-aminoalk-2-enals 1 react with alkyl- or arylthiols to give unexpected thioesters of α-amino acid 3 in good yields. The same type of product is formed when substrate 1b is treated with ethane-1,2-dithiol. The reaction proceeds via an intermediate 1,2-adduct which is transformed, after a 1,3-shift, into the final thioester 3.