Chiral 2-acetamidoacrylates in conjugate addition – asymmetric enolate trapping reactions. Asymmetric synthesis of phenylalanine
Open Access
- 1 September 1992
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 70 (9) , 2325-2328
- https://doi.org/10.1139/v92-294
Abstract
A new route to the asymmetric synthesis of α-amino acids based on the reactivity of chiral 2-acetamidoacrylates with nucleophiles through a conjugate addition followed by diastereoselective protonation of the enolate is described. Phenylalanine precursors are obtained in excellent chemical yields (80–95%) with moderate diastereomeric excess (0–44%) through the reaction of chiral 2-acetamidoacrylates with phenylmagnesium bromide in the presence of CuI followed by diastereoselective enolate protonation.Keywords
This publication has 0 references indexed in Scilit: