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In contrast, the addition of dialkylzincs to ferrocene -1,1′-dicarbaldehyde in the presence of a chiral catalyst proved to be very limited due to interactions of the alcoholate obtained after mono-addition and the remaining aldehyde function leading to low enantiomeric excess and considerable amounts of meso-diol (S. Vettel, unpublished results, Marburg 1994). Compare with a successful approach using N,N-dialkylnorephedrines as chiral catalysts: Soai, K.; Hayase, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908.
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NMR-spectroscopy of the crude reaction mixture of 9b indicates ca. 95 % selectivity for the directed metallation. Recrystallization from t-BuOMe affords the pure enantiomer 9b.
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