Rediscovery, Isolation, and Asymmetric Reduction of 1,2,3,4-Tetrahydronaphthalene-1,4-dione and Studies of Its [Cr(CO)3] Complex


  • Support of this work by the Swiss National Foundation is gratefully acknowledged (SNF grant 200020-103851).


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For 25 years it has been known that 1,4-dihydroxynaphthalene and tetrahydronaphthalene-1,4-dione coexist as stable tautomers; however, the dione has now emerged as an interesting starting material for synthesis. Its efficient isolation is reported, and the corresponding [Cr(CO)3] complexes of the two tautomers are prepared, thus leading to efficient desymmetrization using chiral diamine acyl-transfer catalysts (see scheme).