Tetrahedron

An asymmetric synthesis of l-[3-13 C] phenylalanine and l-[3-13 C] tyrosine from [13 C] carbon monoxide

K Takatori, M Nishihara, Y Nishiyama, M Kajiwara

Index: Takatori, Kazuhiko; Nishihara, Mikiko; Nishiyama, Yukie; Kajiwara, Masahiro Tetrahedron, 1998 , vol. 54, # 52 p. 15861 - 15869

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Citation Number: 21

Abstract

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 ...