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Synthesis 1994; 1994(9): 911-912
DOI: 10.1055/s-1994-25600
short paper
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(1S,2R,3R,4R)-α,α,α′,α′-Tetraphenylbicyclo [2.2.1]heptane-2,3-dimethanol and Its Enantiomer as Ligands in Titanate-Complex-Catalyzed Diethylzinc Addition to Aldehydes

Claus Dreisbach* , Udo Kragl, Christian Wandrey
  • *Research Center Jülich, Institute of Biotechnology, D-52425 Jülich, Germany
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Publikationsdatum:
17. September 2002 (online)

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Starting from (1S,2R,3R,4R)-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid (1) and its enantiomer ent-1 the title compounds 3 and ent-3 were synthesized in 74% yield. They were used in asymmetric synthesis for the first time. The titanate-complex-catalyzed addition of diethylzinc to aldehydes was chosen as a model system for testing the catalytic properties of 3. The resulting alcohols 4 could be obtained with up to 97.7% enantiomeric excess.