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Synthesis 2000; 2000(1): 135-138
DOI: 10.1055/s-2000-6240
DOI: 10.1055/s-2000-6240
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Efficient Enantioselective Synthesis of Cα-Methyl Aspartic Acid and 3-Amino-3-methylpyrrolidin-2-one
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Publication Date:
31 December 2000 (online)
The asymmetric dipolar cycloaddition reaction of Me3SiCHN2 and auxiliary-bound methacrylate affords ready entry into optically active substituted pyrazolines. Herein we disclose an unusual alkaline fragmentation reaction of optically active pyrazoline 1 that affords an efficient synthesis of the pharmacologically important 2-methylaspartic acid in good yields. Additionally, in an alternative transformation of the pyrazoline (1), reductive cleavage provides the corresponding 3-amino-3-methylpyrrolidin-2-one.
amino acids - pyrazolines - asymmetric synthesis