Download PDF
Synlett 2000; 2000(12): 1699-1707
DOI: 10.1055/s-2000-8668
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >