Stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and (7S,8R)-7-N-benzylaminopyrrolizidin-3-one

Article abstract of DOI:10.1016/S0040-4039(97)10749-3

The highly stereoselective synthesis of (2S,3S)-3-N-benzylaminoprolinol and derivatives involved the conjugate addition of N-benzylamine to α,β-unsaturated lactam 2. Wittig-Horner reactions with 1-acetyl-3-N-acetyl-N-benzylaminoprolinal provided a simple access to (7S,8R)-7-N-benzylaminopyrrolizidin-3-one.