Download PDF
Synlett 1999; 1999(S1): 925-929
DOI: 10.1055/s-1999-3093
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.

The Novel Sequence Diels-Alder Reaction/Ireland-Claisen Rearrangement Applied to Acyclic Dienophiles: New Insights into the Selectivity of the Ireland-Claisen Rearrangement

Jörg Velker* , Jean Philippe Roblin, Antonia Neels, Ana Tesouro, Helen Stoeckli-Evans, Frank-Gerrit Klaerner, Jan-Stefan Gehrke, Reinhard Neier
  • *Laboratoire de chimie de synthèse et de chimie biomimetique, Institut de Chimie, Av. Bellevaux 51, CH-2000 Neuchâtel, Switzerland; Fax +41(32)7 18 25 11; E-mail: Reinhard.Neier@ICH.UNINE.CH; Website: http://www.unine.ch/chim/nei1.html
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

The new dienes 4a-d, 7 and 11 reacted in good yields with acyclic dienophiles like methyl acrylate and diethyl fumarate in the tandem process Diels-Alder reaction/Ireland-Claisen rearangement. Analysis of the relative configuration of products 5, 6, 8-10 and 12 indicated that preference for the chair or boat transition state of the Ireland-Claisen rearrangement is stronlgy influenced by the relative configuration of the substituents of the cyclohexene ring.

Diels-Alder reaction - Ireland-Claisen rearrangement - tandem reaction - diastereoselectivity - high pressure