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Synthesis 1992; 1992(5): 433-435
DOI: 10.1055/s-1992-26126
short paper
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The Atropo-Enantioselective Ring Opening of Achiral Lactone-Bridged Biaryls Using Chirally Modified Aluminum Hydrides

Gerhard Bringmann* , Thomas Hartung
  • *Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-8700 Würzburg, Germany
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Publication Date:
17 September 2002 (online)

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The atropo-enantioselective preparation of the chiral biaryl 2-hydroxymethyl-1-(2-hydroxy-4, 6-dimethoxyphenyl)naphthalene (7) from 1,3-dimethoxy-6H-benzo [b]naphtho[1,2-d]pyran-6-one (3) is described, whereby two formal problems of stereoselective biaryl synthesis are independently solved: The carbon-carbon bond formation by the intramolecular aryl coupling of the ester-type prefixed aromatic halves, and the asymmetric induction at the pre-formed biaryl axis by the subsequent stereoselective ring-opening reaction, using chiral hydrogen nucleophiles.