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A novel and general route for the solid phase synthesis of N-substituted α-amino acids has been developed. This synthesis employs Fukuyama's 2-nitrobenzenesulfonamide protecting group for preparation of secondary amines. The versatility of this methodology is demonstrated by the facile synthesis of a trisubstituted diketopiperazine (DKP) skeleton.
A systematic study has been completed demonstrating the utility and scope of the potassium dichromate-mediated oxidative cleavage of enamines. Among the methods studied, the biphasic, chromic acid-diethyl ether conditions gave the best results and prevented over-oxidation of the carbonyl products. This method is general for β, β-disubstituted enamines, such as (1E)-1-(4-morpholino)-2-phenyl-2-methyl-1-propene,...
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