An asymmetric synthesis of l-[3-13C]phenylalanine and l-[3-13C]tyrosine from [13C]carbon monoxide
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Add time:08/31/2019 Source:sciencedirect.com
l-[3-13C]Phenylalanine and l-[3-13C]tyrosine were synthesized. [α-13C]Benzyl bromides were prepared from [13C]carbon monoxide via the palladium-catalyzed carboalkoxylation of aryl halides. The asymmetric carbon corresponding to the 2-position in phenylalanine was introduced by the diastereoselective alkylation of Dellaria's oxazinone with [α-13C]benzyl bromides. Finally, ethanolysis, deprotection, hydrogenolysis and acid hydrolysis of the resulting alkylated oxazinones gave l-[3-13C]phenylalanine and l-[3-13C]tyrosine in high optical purity.
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