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Asymmetric synthesis with chiral beta lactams alpha substituted aromatic alpha amino acids and their derivatives through highly stereoselective alkylations



Asymmetric synthesis with chiral beta lactams alpha substituted aromatic alpha amino acids and their derivatives through highly stereoselective alkylations



Journal of the American Chemical Society 110(1): 278-281



A novel route to optically pure .alpha.-alkylated aromatic .alpha.-amino acids and their dipeptide derivatives was developed through the asymmetric alkylation at the C-3 position of a chiral .beta.-lactam 1 followed by the reductive cleavage of the alkylated .beta.-lactams 2. The stereochemical course of the reaction is effectively controlled by the chiral center at the C-4 position of the .beta.-lactam. This novel asymmetric alkylation was successfully applied for the synthesis of (S)-.alpha.-methyl-DOPA via a chiral .beta.-lactam 4, which was synthesized by the asymmetric [2 + 2] cycloaddition of a chiral ketene to an imine.

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Accession: 004792392

Download citation: RISBibTeXText

DOI: 10.1021/ja00209a044


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