Stereocontrolled addition reaction of organometallics to chiral. ALPHA.-keto amides.

…, Y Ukaji, M Funabora, M Yamashita, T Sato

Index: Fujisawa, Tamotsu; Ukaji, Yutaka; Funabora, Makoto; Yamashita, Mikio; Sato, Toshio Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 7 p. 1894 - 1897

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Citation Number: 27

Abstract

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.