Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Diastereofacial Discrimination in the Reaction of Chiral Alkoxymethyl Oxime Ethers with Allyl Metallic Reagents
Yutaka UkajiKouji KumeToshiyuki WataiTamotsu Fujisawa
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1991 Volume 20 Issue 1 Pages 173-176

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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.

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© 1991 The Chemical Society of Japan
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