The Paterno-Buchi reaction of N-acyl enamines and aldehydes - The development of a new synthetic method and its application to total synthesis and molecular recognition studies

The Paterno-Buchi reaction of aldehydes and N-acyl or N-alkoxycarbonyl enam ines represents a short and efficient method for the stereoselective synthe sis of cis-3-aminooxetanes. Consecutive ring opening reactions facilitate t he preparation of cyclic and acyclic 1,2-amino alcohols. The application of a photocycloaddition/ring opening sequence to the synthesis of an enantiom erically pure pyrrolidinol alkaloid is discussed. The use of cyclic NH-acid ic lactams as alkene components in the photocycloaddition allows the study of host-guest interactions. An achiral guest can be attached to a chiral ho st by two hydrogen bonds in such a way that a dis- crimination of enantioto pic faces is possible. 1 Introduction 2 Initial Experiments 3 The Synthesis of 3-Aminooxetanes and their Ring Opening Reactions 4 Facial Diastereoselectivity in Cyclic Enamides: The Synthesis of (+)-Preu ssin 5 Hydrogen Bonding as a Means to Control the Facial Stereoselectivity in th e Paterno-Buchi Reaction.