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Synlett 2000; 2000(12): 1699-1707
DOI: 10.1055/s-2000-8668
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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

T. Bach*
  • *Lehrstuhl für Organische Chemie der TU München, Lichtenbergstr. 4, 85747 Garching, Germany; Fax +49(0)89/28 91 33 15; E-mail: thorsten.bach@ch.tum.de
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Publikationsdatum:
31. Dezember 2000 (online)

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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