Diastereofacial Control in the Reaction of Chiral α-Amino Ketones with Several Organometallics
- 5 January 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 17 (1) , 59-62
- https://doi.org/10.1246/cl.1988.59
Abstract
The addition reaction of organometallics to chiral α-amino ketones, prepared from α-halo ketones and (S)-2-methoxymethylpyrrolidine as a chiral auxiliary, gave different diastereomers of chiral amino alcohols depending on the difference of coordination ability of the metal used, i.e. organometallics such as Grignard reagent, organozinc, and cerium reagents preferred re-face attack, while organolithium compound attacked from si-face.Keywords
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