501331-01-7Relevant academic research and scientific papers
Efficient synthesis of enantiomerically pure β2-amino acids via chiral isoxazolidinones
Lee, Hee-Seung,Park, Jin-Seong,Kim, Byeong Moon,Gellman, Samuel H.
, p. 1575 - 1578 (2007/10/03)
We report a practical and scalable synthetic route for the preparation of α-substituted β-amino acids (β2-amino acids). Michael addition of a chiral hydroxylamine, derived from α-methylbenzylamine, to an α-alkylacrylate followed by cyclization gives a diastereomeric mixture of α-substituted isoxazolidinones. These diastereomers are separable by column chromatography. Subsequent hydrogenation of the purified isoxazolidinones followed by Fmoc protection affords enantiomerically pure Fmoc-β2-amino acids, which are useful for β-peptide synthesis. This route provides access to both enantiomers of a protected β2-amino acid.
