The Paternò-Büchi Reaction of N-Acyl Enamines and Aldehydes - The Development of a New Synthetic Method and its Application to Total Synthesis and Molecular Recognition Studies
31 December 2000 (online)
The Paternò-Büchi reaction of aldehydes and N-acyl or N-alkoxycarbonyl enamines represents a short and efficient method for the stereoselective synthesis of cis-3-aminooxetanes. Consecutive ring opening reactions facilitate the preparation of cyclic and acyclic 1,2-amino alcohols. The application of a photocycloaddition/ring opening sequence to the synthesis of an enantiomerically pure pyrrolidinol alkaloid is discussed. The use of cyclic NH-acidic lactams as alkene components in the photocycloaddition allows the study of host-guest interactions. An achiral guest can be attached to a chiral host by two hydrogen bonds in such a way that a discrimination of enantiotopic faces is possible.
photochemistry - cycloadditions - stereoselective synthesis - ring opening