Diastereofacial Discrimination in the Reaction of Chiral Alkoxymethyl Oxime Ethers with Allyl Metallic Reagents
- 1 January 1991
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 20 (1) , 173-176
- https://doi.org/10.1246/cl.1991.173
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.Keywords
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