Download PDF
Synlett 1991; 1991(8): 581-583
DOI: 10.1055/s-1991-20805
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.

Diastereoselective Ring Opening of Achiral Bridged Biaryls Using Chiral O- and N-Nucleophiles: First Atropo-Enantioselective Synthesis of (-)-4,4′-Bis(orcinol)1

Gerhard Bringmann* , Rainer Walter, Christian L. J. Ewers
  • *Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-8700 Würzburg, Germany
Further Information

Publication History

Publication Date:
07 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The atropisomer-selective cleavage of the bridged biaryl 1 (3,8,10-trimethoxy-1-methyldibenzo[b,d]pyran-6-one), which has no stereogenic element, is described. The directed ring opening of the lactone bridge is achieved with chiral O- or N-nucleophiles, i.e. by external asymmetric induction. The application of this novel process to the first atropoenantioselective synthesis of the constitutionally symmetrical, known (-)-4,4′-bis(orcinol) 5 (6,6′-dimethyl-2,2′,4,4′-biphenyltetrol) is described.

      >