Hydrolysis and carbonyl hydration of adamantane‐based twisted amide 1 were studied computationally. The importance of the bridgehead methyl substituents on these reactions was determined. The carbonyl hydration of 1 is structurally and energetically much like the hydration of a transition state to amide CN bond rotation. However, hydrolysis of 1 to the amino acid is dependent on the bridgehead methyl substituents and less like hydrolysis of an amide transition state.
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Morgan et al. (2004) studied this question.
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