117834-01-2Relevant academic research and scientific papers
Synthesis of Chiral Vinylglycines
Beaulieu, Pierre L.,Duceppe, Jean-Simon,Johnson, Carolyne
, p. 4196 - 4204 (2007/10/02)
(R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8.Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (>95percent ee) and double-bond geometry.D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives β,γ-unsaturated amino acids with the L configuration.The double-bond geometry is controlled by the nature of the phosphorous ylide employed.The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.
