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

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Abstract

The Paterno-Buchi 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. 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 (+)-Preussin 5. Hydrogen Bonding as a Means to Control the Facial Stereoselectivity in the Paterno-Buchi Reaction.

Original languageEnglish
Pages (from-to)1699-1707
Number of pages9
JournalSynlett
Issue number12
StatePublished - 2000

Keywords

  • Cycloadditions
  • Photochemistry
  • Ring opening
  • Stereoselective synthesis

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