Download PDF
Synlett 1999; 1999(10): 1654-1656
DOI: 10.1055/s-1999-2892
letter
© 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.

Synthesis of Bis(enolnonaflates) and their 4-exo-trig-Cyclizations by Intramolecular Heck Reactions

Stefan Bräse*
  • *Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Straße, D-52074 Aachen, Germany; Fax + (49) (0)2 41/8 88 81 27; E-mail: Braese@oc.RWTH-Aachen.de
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

Starting from dimedone, novel 1,3-bis(enolnonaflates) (nonafluorobutanesulfonates) have been prepared in four efficient steps. Cyclization of these 1,5-hexadienes under Palladium catalysis proceeded cleanly to give bicyclo[4.2.0]octadienes and bicyclo[4.2.0]octenones, respectively, by an unprecedented 4-exo-trig process. Insertion in one enolsulfonate moiety, intramolecular cyclization and subsequent second insertion after intermolecular reaction with alkenes (acrylates) or alkynes (3,3-dimethylbutyne) led to novel, highly congested hydrocarbons. Application of a chiral catalyst system resulted in modest asymmetric induction to furnish an enantioselective Heck-type desymmetrization reaction product.

asymmetric Heck reaction - cyclobutanes - cascade reaction - desymmetrization

      >