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

Abstract

AbstractL‐[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 © 2004 John Wiley & Sons, Ltd.