Enantioselective synthesis of .beta.-amino acids. 4. 1,2 Asymmetric induction in the alkylation of 1-benzoyl-3,6(S)-dimethylperhydropyrimidin-4-one. Preparation of the like and unlike stereoisomers of 2-methyl- and 2-benzyl-3(S)-aminobutanoic acid

作者: Eusebio Juaristi , Jaime Escalante

DOI: 10.1021/JO00060A051

关键词: Methyl iodideAmino acidAlkylationBenzyl bromideAsymmetric inductionSchiff baseEnantioselective synthesisDiastereomerStereochemistryChemistry

摘要: The title perhydropyrimidin-4-one (S)-4 was prepared from (S)-3-aminobutanoic acid via the Schiff base (S)-8. This heterocycle alkylated (LDA, methyl iodide, or benzyl bromide) to afford like and unlike diastereomeric products in a 80:20 ratio. Separation hydrolysis (6 N aqueous HCl) of these 5,6-dialkylperhydropyrimidin-4-ones leads free, enantiomerically pure, amino acids 11-14

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