E. Juaristi, D. Quintana, B. Lamatsch
Mar 1, 1991
Citations
0
Influential Citations
58
Citations
Journal
Journal of Organic Chemistry
Abstract
β-Alanine, an inexpensive α-amino acid, was converted into the 2-tert-butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high diastereoselectivity via the corresponding enolate. The high stereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C(2), which directs addition from the enolate face opposite to this group. The hydrolysis of the resulting adducts proceeds with 6N hydrochloric acid to afford α-substituted β-amino acids in good yields. These results pave the road to the development of a new asymmetric synthesis of enantiomerically pure α-substituted β-amino acids