Chiral N-phosphonyl imine chemistry: asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines
Chiral N-phosphonyl imine chemistry: asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines
复制标题
DOI：
10.1007/s11426-010-0026-y
复制
发表时间：
2010-01-01
影响因子：
9.6
通讯作者：
Li GuiGen
中科院分区：
文献类型：
--
作者：
Ai Teng;Pindi, Suresh;Li GuiGen
在方便的反应条件下，以较高的收率合成了以二苯胺为基，通过助剂中的N-异丙基连接的膦酰亚胺。这些新的手性N-膦酰亚胺与甘氨酸烯醇化物反应，可顺利地得到手性α-β-二氨基酯，产率为72%-90%，非对映选择性>99：1dr。通过用HBr处理，可以容易地除去手性助剂。通过将产物转化为已知样品，已明确确定了绝对结构。
Diphenyl diamine-based phosphonyl imines attached by the N-isopropyl group in the auxiliary have been synthesized in good yields under convenient reaction conditions. These new chiral N-phosphonyl imines can react with glycine enolate smoothly to give chiral alpha-beta diamino esters in good yields (72%-90%) and up to excellent diastereoselectivity (>99:1 dr). By treatment with HBr, the chiral auxiliary can be readily removed. The absolute structure has been unambiguously determined by converting a product to a known sample.