Efficient Synthesis of 1-Azadienes Derived from α-Aminoesters. Regioselective Preparation of α-Dehydroamino Acids, Vinylglycines, and α-Amino Acids
作者:Francisco Palacios、Javier Vicario、Domitila Aparicio
DOI:10.1021/jo061140f
日期:2006.9.1
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
通过磷腈与β,γ-不饱和α-酮酸酯的aza-Wittig反应,可以有效合成α-氨基酯衍生的1-azadienes。这些官能化的1-氮二烯的区域选择性1,2-还原得到乙烯基甘氨酸衍生物,而共轭的1,4-还原得到α-脱氢氨基酸化合物。碳-碳和亚胺-碳-氮双键的还原都会导致α-氨基酸衍生物的形成。