Alternative procedure for the synthesis of enantiopure 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one, a useful starting material for the enantioselective synthesis of α-substituted β-amino acids

✍ Scribed by Martı́n A. Iglesias-Arteaga; Elena Castellanos; Eusebio Juaristi

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 177 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00048-x

✦ Synopsis

The title heterocycle is prepared in enantiomerically pure form and in 46-50% overall yield from (S)-asparagine, a readily available starting material. The synthetic route described in this report represents a major improvement over the original procedure (Tetrahedron: Asymmetry 1991, 3, 723), that afforded a 24-32% overall yield. Furthermore, the use of toxic reagents such as Pb(OAc) 4 and dimethyl sulfate is avoided in the present protocol.