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

✍ Scribed by Kazuhiko Takatori; Akira Hayashi; Masahiro Kajiwara

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: French
• Weight: 119 KB
• Volume: 47
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.868

✦ Synopsis

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 of the double bond with diimide, removal of the chiral auxiliary, and hydrolysis gave L‐[4‐^13^C]lysine (2). Copyright © 2004 John Wiley & Sons, Ltd.