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Paper | Regular issue | Vol 34, No. 2, 1992, pp.349-355
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5930
Use of Chiral Amidals in the Synthesis of 6-Methylperihydropyrimidin-4-ones, Protected Form of β-Amino Acids

Rosa Amoroso, Giuliana Cardillo,* and Claudia Tomasini

*Dipartimento di Chimica "G. Giamician", Università di Bologna, Centro per lo Studio della Fisica delle Macromolecole, via Selmi 2, 40126 Bologna, Italy


The synthesis of 6-methylperihydropyrimidin-4-ones (7a and 7b) is described by mercury cyclization of the β,γ-unsaturated amidal (3). After reduction of the intermediate organomercury compound (6) and separation of the diastereomeric mixture, the perihydropyrimidin-4-ones (7a and 7b) have been obtained. Their structure has been fully characterized by means of 1H nmr spectroscopy and, after acid hydrolysis, the 3-aminobutyric acids (8a and 8b) have been obtained.