Diels‐Alder reaction of cyclopentadiene and methyl N‐carbobenzyloxy‐2‐iminoacetate generated in situ from methyl 2‐chloro‐N‐carbobenzyloxyglycinate by triethylamine gave the N‐carbobenzyloxy unsaturated bicyclic proline ester. This was converted in two steps to 2‐azabicylo[2.2.1]heptane‐3‐carboxylic acid. In contrast to N‐carbobenzyloxy‐L‐proline methyl ester, the corresponding bicyclic proline ester was resistant to hydrolysis catalyzed by carboxypeptidase Y.
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Gaitanopoulos et al. (1985) studied this question.
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