Stereospecific synthesis of alpha-methylated amino acids.
Both 2,5-trans and 2,5-cis disubstituted 2-tert-butyl-5-(indol-3-yl)methylimidazolidin-4-ones were synthesised and their enolates were prepared using LDA. While the enolate of the 2,5-trans disubstituted derivative could not be methylated, the enolate of the cis-2,5-disubstituted derivative was successfully methylated with methyl iodide to a product which on hydrolysis gave enantiomerically pure alpha-methyl-L-tryptophan.
Mzengeza
S
S
Montreal Neurological Institute and Department of Neurology and Neurosurgery, McGill University, Canada.
Venkatachalam
T K
TK
Diksic
M
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000378:metabolism*; D008745:Methylation; D008956:Models, Chemical; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*
D000596:Amino Acids; C020774:alpha-methyltryptophan; D014364:Tryptophan