Enantioselective synthesis of. beta.-amino acids. 2. Preparation of the like stereoisomers of 2-methyl-and 2-benzyl-3-aminobutanoic acid

…, J Escalante, B Lamatsch, D Seebach

Index: Juaristi, Eusebio; Escalante, Jaime; Lamatsch, Bernd; Seebach, Dieter Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2396 - 2398

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Citation Number: 70

Abstract

An improved procedure for the preparation of (R)-and (S)-3-aminobutanoic acids (2a) through diastereomer separation of the correaponding (1'8-N-phenethyl derivatives 1 is reported. From 2a, the four poasible stereisomeric perhydropyrimidin-4-ones 4 were prepared through the amide 2c and the Schiff base 3. In the cyclization of 3, the ciaproducts 4 predominate ca. 95: 5. These heterocycles can be alkylated (LDA, RX), as demonstrated ...