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N-Methylation of adamantane-substituted oxalamide unit affects its conformational rigidity: Askew conformation of the oxalamide brigde

The synthesis of adamantane functionalized retropeptides, N, N´-bis(2-adamantyl-2-carboxylic acid methyl ester)oxalamide (1) and N-methyl-N, N´-bis(2-adamantyl-2-carboxylic acid methyl ester)oxalamide (2), as well as the influence of the N-methylation on the conformational preferences of oxalamide group are described. In th solid state the oxalamide group of 1 is planar while in the retropeptide 2 adopts a skew-conformation.

adamantane ; N-methylation ; oxalamides ; X-ray structure

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