Download PDF
Synlett 1992; 1992(4): 281-282
DOI: 10.1055/s-1992-21339
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.

Enantioselective Intramolecular Hetero Diels-Alder Reactions of 1-Oxa-1,3-butadienes with a New Chiral Lewis Acid1

Lutz F. Tietze* , Peter Saling
  • *Institut für Organische Chemie, Universität Göttingen, Tammannstr. 2, D-3400 Göttingen, Germany
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The intramolecular hetero Diels-Alder reaction of 1-oxa-1,3-butadienes 3a-g, obtained in situ by a Knoevenagel condensation of aromatic aldehydes 1a-g and N,N′-dimethylbarbituric acid (2), was studied in the presence of a new chiral titanium Lewis acid (5) which has 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose as a ligand. Depending on the reaction conditions and the substituents on the aromatic ring system, the cis-fused tetracycles 4a-g were formed with ee-values up to 88%. This is the first example of an enantioselective intramolecular hetero Diels-Alder reaction.

      >