Asymmetric synthesis of L??[4??13C] lysine by alkylation of oxazinone derivative as a chiral glycine equivalent

…, A Hayashi, M Kajiwara

Index: Takatori, Kazuhiko; Hayashi, Akira; Kajiwara, Masahiro Journal of Labelled Compounds and Radiopharmaceuticals, 2004 , vol. 47, # 11 p. 787 - 795

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Citation Number: 5

Abstract

Abstract L-[4-13 C] Lysine (2) was synthesized from sodium [2-13 C] acetate (3) and Dellaria's oxazinone 1 as a chiral glycine equivalent. Wittig reaction of the glycinal 7 and 13 C-labeled phosphonium ylide 5, prepared from sodium [2-13 C] acetate (3), gave the α, β- unsaturated ester 8. The ester 8 was converted to the allylic bromide 10. Alkylation of the oxazinone 1 with 10 proceeded with high diastereoselectivity. Ethanolysis, hydrogenation ...