ChemInform Abstract: An Asymmetric Synthesis of L-[3-13C]Phenylalanine and L-[3-13C]Tyrosine from [13C]Carbon Monoxide

Autor:	Yukie Nishiyama, Mikiko Nishihara, Kazuhiko Takatori, Masahiro Kajiwara
Rok vydání:	2010
Předmět:	chemistry.chemical_compound chemistry Hydrogenolysis Asymmetric carbon Aryl Enantioselective synthesis Phenylalanine General Medicine Tyrosine Alkylation Medicinal chemistry Carbon monoxide
Zdroj:	ChemInform. 30
ISSN:	1522-2667 0931-7597
Popis:	l -[3- 13 C]Phenylalanine and l -[3- 13 C]tyrosine were synthesized. [α- 13 C]Benzyl bromides were prepared from [ 13 C]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- 13 C]benzyl bromides. Finally, ethanolysis, deprotection, hydrogenolysis and acid hydrolysis of the resulting alkylated oxazinones gave l -[3- 13 C]phenylalanine and l -[3- 13 C]tyrosine in high optical purity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::64833f5d375aa80319e845ed4b3047d8 https://doi.org/10.1002/chin.199917219 Zobrazit plný text záznamu Plný text