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Synlett 1991; 1991(8): 581-583
DOI: 10.1055/s-1991-20805
DOI: 10.1055/s-1991-20805
letter
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Diastereoselective Ring Opening of Achiral Bridged Biaryls Using Chiral O- and N-Nucleophiles: First Atropo-Enantioselective Synthesis of (-)-4,4′-Bis(orcinol)1
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Publikationsverlauf
Publikationsdatum:
07. März 2002 (online)
![](https://www.thieme-connect.de/media/synlett/199108/lookinside/thumbnails/10.1055-s-1991-20805-1.jpg)
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.