118743-83-2Relevant articles and documents
Asymmetric Syntheses of the Naturally Ocurring β-Amino Acids, β-Lysine, β-Leucine and β-Phenyl-β-alanine via Nitrone Cycloaddition
Keirs, David,Moffat, David,Overton, Karl,Tomanek, Richard
, p. 1041 - 1051 (2007/10/02)
A general asymmetric synthesis of β-amino acids is based on the dipolar cycloaddition of nitrones 7 (R* chiral) with vinyl acetate 8a, ketene acetals 8b or α-chloroacrylonitrile 8c.The cycloadducts 9 are converted either directly (9b) or via the isoxazolidones 10 (9a, 9c) into the free β-amino acids 11.Diastereoselectivity at C-3 in the adducts 9 ranges between 2:1 and 11:1.The natural β-amino acids, β-lysine, β-leucine and β-phenyl-β-alanine, have been prepared in this way.