N—烷基化氨基酸和氨基酸酯的一步反应

旋光性氨基酸或其酯室温下在NaHTe/EtOH和NaHTe/H_2O体系中与羰基化合物反应,一步得到N-烷基化氨基酸或其酯。具有二级胺基的脯氨酸苄酯亦能高产率生成N-Bzl-L-Pro·OEt。反应条件温和,不发生外消旋化,适用于带有各种基团的氨基酸。

Study on a New One-step Reductive N-Alkylation of Amino Acids and Their Esters

Ten new N-alkylated amino acid esters were prepared at room temperature. It gave good to excellent yields. The reductive animation reactions of unesterified amino acids. especially the amino acids being soluble in water, proceed smoothly, when the reduction was carried out with heating in ethanol or water. It should be noted that reaction product of the secondary amino group of proline ester with benzaldehyde was smoothly reduced to N-Bzl-L-ProOEt under the usual condition. The method can be widely exploited for various amino acids and biologically important nitrogen containing natural products.