Download PDF
Synlett 1995; 1995(11): 1174-1176
DOI: 10.1055/s-1995-5196
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.

Efficient Palladium-Catalyzed Chirality Transfer in Allyl Carbonates. An Approach to β-Aryl-Substituted γ-Lactones and γ-Hydroxy Amides. Synthesis of the Antidepressant (R)-Rolipram®

Manfred Braun* , Kersten Opdenbusch, Claudia Unger
  • *Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany, Fax 49-(0)211-311-3085; Internet braunm@clio.rz.uni-duesseldorf.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Allyl carbonates 7 are readily available in high enantiomeric and diastereomeric purity by addition of vinyllithium reagent 3b to aldehydes. Palladium-catalyzed allylic substitution provides a chirality transfer so that carbonates 7 are converted into malonates 8 which serve as intermediates for the synthesis of lactones (R)-10, amides (R)-11, and lactam (R)-14 (Rolipram®).

palladium catalysis - allylic substitution - enantiopure compounds - (R)-Rolipram®

      >