Complementary stereoselection in the addition reaction of several organometallics to chiral benzoylformamide, prepared from benzoylformic acid and (S)-2-(methoxymethyl)pyrrolidine, could be achieved using magnesium- and titanium-based reagents to give differeent diastereomers of atrolactamide. On the other hand, the reaction of phenyl metallics to the corresponding pyruvamide afforded (S)-atrolactamide.
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Fujisawa et al. (1990) studied this question.
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