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Synthesis of 2-Substituted-5-halo-2,3-dihydro-4( H )-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids

2007; American Chemical Society; Volume: 72; Issue: 13 Linguagem: Inglês

10.1021/jo0705115

1520-6904

B.R. Diaz-Sanchez, Martín A. Iglesias‐Arteaga, R. Melgar‐Fernandez, Eusebio Juaristi,

Multicomponent Synthesis of Heterocycles

A convenient, one-pot procedure for the synthesis of 1-benzoyl-2(S)-substituted-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by tandem decarboxylation/β-iodination of the corresponding 6-carboxy-perhydropyrimidin-4-ones was developed. In addition, several 1-benzoyl-2(S)-substituted-5-bromo-2,3-dihydro-4(H)-pyrimidin-4-ones were readily prepared by bromination of 1-benzoyl-2(S)-substituted-2,3-dihydro-4(H)-pyrimidin-4-ones. Subsequently, Sonogashira coupling of the halogenated heterocyclic enones with various terminal alkynes produced 1-benzoyl-2(S)-isopropyl-5-alkynyl-2,3-dihydro-4(H)-pyrimidin-4-ones in good yields. Hydrogenation of the unsaturated C−C moieties in the Sonogashira products followed by acid hydrolysis afforded highly enantioenriched α-substituted β-amino acids.