Tetrahedron Letters p. 5257 - 5260 (1990)
Update date:2022-08-02
Topics:
Alks, Vitauts
Sufrin, Janice R.
A synthetic route to L-2-amino-4-methoxy-trans-but-3-enoic acid, exclusive of the cis-isomer, has been developed. The key step is direct formation of a trans-enol ether derivative from the corresponding dimethylacetal, by refluxing in CCl4, in the presence of hexamethyldisilazane and Me3SiI. The isomeric L-cis amino acid could be accessed from this route by isomerizing the intermediate, methyl DL-2-acetamido-2-amino-4-methoxy-trans-but-3-enoate at 217° C to give cis-trans mixture in a 1:10 ratio.
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