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A series of chiral δ‐diamines and structurally analogous δ‐amino alcohols derived from natural tartaric acid were synthesized and a comparative study of their activity and selectivity in the enantioselective alkylation of aromatic aldehydes was carried out. Our results show that in general the δ‐diamines were found to be better chiral inducers than the corresponding δ‐amino alcohols. The highest selectivity was observed when benzaldehyde was alkylated in the presence of the benzylic diamine, giving ( R )‐1‐phenylpropanol with an ee of 42%.
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Serra et al. (2008) studied this question.
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