855206-49-4Relevant articles and documents
Asymmetric synthesis of L-[4-13C]lysine by alkylation of oxazinone derivative as a chiral glycine equivalent
Takatori, Kazuhiko,Hayashi, Akira,Kajiwara, Masahiro
, p. 787 - 795 (2004)
L-[4-13C]Lysine (2) was synthesized from sodium [2- 13C]acetate (3) and Dellaria's oxazinone 1 as a chiral glycine equivalent. Wittig reaction of the glycinal 7 and 13C-labeled phosphonium ylide 5, prepared from sodium [2-13C]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 of the double bond with diimide, removal of the chiral auxiliary, and hydrolysis gave L-[4- 13C]lysine (2). Copyright
