Concise Synthesis of N-Boc-2,3-methanoproline Methyl Ester

Schimmel/Conrades Science Center Atrium

Conformational rigidification through the incoporation of bicyclic ring systems constitutes a useful strategy for elucidating structure/function relationships. A two-step synthesis of a fully protected proline derivative, N-Boc-2,3-methanoproline methyl ester, has been accomplished via an intramolecular ring-closing reaction. The racemic product was readily separated using chiral supercritical fluid chromatography. Additional studies using diastereo- and enantiopure reactants were conducted to establish the stereospecificity of this approach, thereby providing insight into the underlying reaction mechanism.