Chemistry Letters

Diastereofacial discrimination in the reaction of chiral alkoxymethyl oxime ethers with allyl metallic reagents.

Y Ukaji, K Kume, T Watai, T Fujisawa

Index: Ukaji, Yutaka; Kume, Kouji; Watai, Toshiyuki; Fujisawa, Tamotsu Chemistry Letters, 1991 , # 1 p. 173 - 176

Full Text: HTML

Citation Number: 20

Abstract

Allyl Grignard reagent complexed with cerium trichloride added to chiral (E)-alkoxymethyl oxime ether, derived from (S)-2-methoxy-1-phenylethanol, to give the corresponding (S)- amine stereoselectively, while the imino addition of allyllithium occurred with a preference for the opposite (R)-isomer. The configuration of the starting oxime ethers was found to greatly influence the diastereofacial discrimination.