Efficient synthesis of 1-azadienes derived from α-aminoesters. Regioselective preparation of α-dehydroamino acids, vinylglycines, and α- amino acids
- Autoría:
- Francisco Palacios, Javier Vicario, Domitila Aparicio
- Año:
- 2006
- Revista:
- The Journal of Organic Chemistry
- Volumen:
- 71
- Página de inicio - Página de fin:
- 7690 - 7696
- Descripción:
-
An efficient synthesis of 1-azadienes derived from α-aminoesters is achieved through an aza-Wittig reaction of phosphazenes with β,γ-unsaturated α-ketoesters. Regioselective 1,2-reduction of these functionalized 1-azadienes affords vinylglycine derivatives, while conjugative 1,4-reduction gives α-dehydroamino acid compounds. Reduction of both the carbon−carbon and the imine−carbon−nitrogen double bonds leads to the formation of α-amino acid derivatives.